WO2011014098A1 - Hydrogenated pyrido[4,3-b]indole derivatives, pharmaceutical composition and methods for the production and use thereof - Google Patents

Hydrogenated pyrido[4,3-b]indole derivatives, pharmaceutical composition and methods for the production and use thereof Download PDF

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Publication number
WO2011014098A1
WO2011014098A1 PCT/RU2010/000274 RU2010000274W WO2011014098A1 WO 2011014098 A1 WO2011014098 A1 WO 2011014098A1 RU 2010000274 W RU2010000274 W RU 2010000274W WO 2011014098 A1 WO2011014098 A1 WO 2011014098A1
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Prior art keywords
indole
ethyl
pyrido
tetrahydro
dimethyl
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PCT/RU2010/000274
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French (fr)
Russian (ru)
Inventor
Валентин Георгиевич НЕНАЙДЕНКО
Владимир Евгеньевич КАБАКОВ
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Общество С Ограниченной Ответственностью "Инномед"
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Publication of WO2011014098A1 publication Critical patent/WO2011014098A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/18—Bridged systems

Definitions

  • This invention relates to new physiologically active derivatives of hydrogenated pyrido [4,3-b] indoles, which exhibit neuroprotective and cognitively stimulating activities that are associated with the interaction of these substances with 5-HT 6 and 5-HT 7 serotonin receptors, butyrylcholinesterase inhibition and exposure on mitochondria, including with the simultaneous effect of these substances on these biological targets.
  • the invention relates to medicinal substances, pharmaceutical compositions containing new derivatives of hydrogenated pyrido [4,3-b] indoles as a drug principle, to new drugs used to treat diseases and conditions of the central nervous system (CNS) of humans and warm-blooded animals.
  • CNS central nervous system
  • the invention also relates to the use of these substances, compositions and preparations in the field of medicine and can be used for the manufacture of neuropharmacological agents for the treatment of neurodegenerative diseases, memory restoration and other cognitive functions lost as a result of pathology, time or adverse effects.
  • the invention can also be used to create new "molecular pharmacological tools)), allowing research (ip vitro and ip viv ⁇ ) of biochemical signal systems and neurochemical mechanisms of the central nervous system.
  • Dementia is currently the most serious medical problem of the elderly, which occurs in 4% of the population aged 65 and at least 35% of the population aged 85 [Ferri CP., Prince M., Waupe S. Wrodatu H., Ftigliopi L., Ganguli M., HaIl K., Hasegawa K., Hendrie H., Huang Y., Jorm A., Mathers C, Mepeses PR, Rimmeg E., Saufsa M; Alzheimer Disase Ipterpatiopl. Globalrevalepse of demetia: and Delphi sceptsus studu. Lapett. 2005; Zbb: 2 ⁇ 2-2 ⁇ 17] ..
  • NMDA receptor antagonist Memantine is also widely used, which leads to a short-term improvement in cognitive functions, but practically does not prevent the progression of B A [Frapsis PT Glutamategos argotaschetoteptompot ofpot apm béhaviulumblemsem conclusionsm. Neurodegepera. Dis. 2008; 5 (5-4): 241-243].
  • 5-HT 6 receptors are modulators of several neurotransmitter systems, including cholinergic, noradrenergic, glutamatergic and dopaminergic [Dawsop L. A., Nguyep HQ, Li P. The 5-HT (6) receptor drug eksitatoru pegotrapsmissiop ip t Kochrrat froptal sortex apd hirrosamrus. Neurosushorhortasologu. 2001; 25: 662-668].
  • the serotonergic system seems to be especially promising as a set of bi-targets for the treatment of AD, since it is involved not only in cognitive functions, but also in the formation of depression, psychosis and aggression - that is, in the manifestation of additional symptoms of AD [Utop N., Khuapg T., Hunter A ., Virleu D. 5-HT6 Resource Pharmaceuticals as Novell Consumer Health Agents for Alzheimer's Disase. Neurothetherareitis. 2008; 5: 458 ⁇ 469].
  • the serotonin 5-HT 7 receptors the antagonists of which are currently considered as possible antidepressants [5-HT 7 , drug therapy, and drug therapy, are the promising additions to 5-HT 6 receptors as biotarriers. . Slipal apd Exhrapetal Rhartasolog apd Rhusiologu. 2007; 34: 546-551].
  • serotonergic system effectors can exhibit cognitively stimulating, antidepressant, and antipsychotic properties.
  • SUBSTITUTE SHEET (RULE 26) drug targets (as, for example, when considering the etiology of AD), a new concept for the search for drugs was developed. Unlike the classical scheme, which implies selective interaction of the active compound with one biological target, the proposed concept of multifunctional drug design takes into account simultaneous interactions with many biological targets. [Vap der Skhuf CJ. Geldenhuys WJ. , Yudim M.V.
  • the authors of the present invention carried out extensive screening studies of compounds of various classes, while leading compounds belonging to the hydrogenated pyrido [4,3-b] indole family were discovered, and then conducted directed synthetic modifications of the detected structures, and as a result, a series of new derivatives of the specified family were obtained that combine the properties of neuroprotectors and cognitive stimuli horov.
  • the new compounds are original and highly effective antagonists of the 5-HT 6 and 5-HT 7 serotonin receptors, butyrylcholinesterase inhibitors and mitochondrial pore blockers.
  • Antagonist means a ligand that binds to receptors of a certain type and does not cause an active cellular response. Antagonists inhibit the binding of agonists to receptors and thereby block the transmission of a specific receptor signal.
  • Dementia means acquired dementia, a persistent decline in cognitive activity with the loss to one degree or another of previously acquired knowledge and practical skills and the difficulty or impossibility of acquiring new ones. Dementia is caused by the breakdown of mental functions that occurs as a result of brain damage, for example, during aging (senile dementia), or as a result of neurodegenerative diseases, for example, in AD.
  • SUBSTITUTE SHEET (RULE 26) Medicinal product (preparation), medicine (d dug, medisi regards) - a substance (or a mixture of substances in the form of a pharmaceutical composition) intended to restore, correct or alter physiological functions in humans and animals, as well as for the treatment and prevention of diseases, diagnosis, anesthesia, contraception, cosmetology and other things.
  • Medicinal substance means a physiologically active substance of synthetic or other (biotechnological, plant, animal, microbial and other) origin, having pharmacological activity and is the active principle of the pharmaceutical composition used for the manufacture and manufacture of a medicinal product (facilities).
  • Mitochondria is an organelle found in many eukaryotic cells and producing ATP, used in the cell as the main source of chemical energy.
  • Neurodegenerative diseases mean specific conditions and diseases characterized by damage and primary death of populations of nerve cells in certain areas of the central nervous system.
  • Neurodegenerative diseases include, but are not limited to, Alzheimer's and Parkinson's; Huntington's disease (chorea); multiple sclerosis; cerebellar degeneration; amyotrophic lateral sclerosis; dementia with Levy bodies; spinal muscular atrophy; peripheral neuropathy; spongiform encephalitis (“bovine rabies”, Creutzfed-Jacob Disase); AIDS-related dementia; multi-infarct dementia; frontotemporal dementia; leukoencephalopathy (a disease of endangered white matter); chronic neurodegenerative diseases; stroke; ischemic, reperfusion, and hypoxic brain damage; epilepsy cerebral ischemia; glaucoma; traumatic brain injury; Down syndrome; encephalomyelitis; meningitis; encephalitis; neuroblastoma; schizophrenia; Depressed
  • neurodegenerative diseases include pathological conditions and disorders that develop with hypoxia,
  • Memory is a property of the central nervous system to absorb information from experience, save it and use it when solving emerging problems.
  • SUBSTITUTE SHEET (RULE 26) Receptors are biological macromolecules located on the cytoplasmic membrane of a cell or intracellular, capable of specifically interacting with a limited set of physiologically active substances (ligands) and transforming the signal about this interaction into a specific cellular response.
  • the signal system means a set of interconnected sequential and parallel molecular processes of regulation of cellular metabolism by external sources of matter and energy that serve as its source.
  • the molecular mechanisms of transmission (transduction) of external signals into the cell mean not only the transmission of signals as such, "but also the whole complex of events associated with it, including amplification, attenuation and suppression (or switching off) of signals.
  • Leader compound means a compound with confirmed maximum physiological activity, found in a series of similar physiologically active substances.
  • the leader compound must also have a set of certain properties that allow it to create a potential medicine (drug-supplement). These properties include selectivity, the absence of toxic effects, as well as a number of physicochemical characteristics that ensure its high bioavailability (for example, compliance with Lipinsky’s rules [Liripski CA., Lombardo F., Dominy BW, Feeney PJ. salubilit apd remebabilit ip drug dissoveg apd devolormpt sttipgs. Adv. Drig Deliv. 2001; 46 (1-3): 3-26]).
  • Pharmacologically acceptable salts mean all salts formed by compounds (bases) and pharmacologically acceptable acids, as inorganic (for example, hydrochloric, sulfuric, phosphoric, etc.); and organic (for example, oxalic, citric, tartaric, maleic, succinic, methyl sulfuric, p-toluenesulfonic acid, etc.).
  • pharmacologically acceptable salts can be formed by compounds (acids) and pharmacologically acceptable bases, while metal salts (sodium, potassium, lithium, calcium, magnesium) and salts of organic bases (for example, various amines, hydroxyalkylamines can be obtained) , basic amino acids, etc.).
  • composition means a composition comprising a drug substance (or several thereof) and at least one of the components selected from the group consisting of pharmaceutically acceptable and pharmacologically compatible excipients, solvents, diluents, carriers,
  • SUBSTITUTE SHEET (RULE 26) auxiliary, distributing and perceiving means, means of delivery, such as preservatives, stabilizers, fillers, grinders, moisturizers, emulsifiers, suspending agents, thickeners, sweeteners, perfumes, flavors, antibacterial agents, fungicides, lubricants, prolonged delivery regulators, the choice and ratio of which depends on the nature and method of administration and dosage.
  • the Central Nervous System means the main part of the nervous system of animals and humans, consisting of an accumulation of nerve cells (neurons) and their processes, represented in invertebrates by a system of closely connected nerve nodes (ganglia), and in vertebrates and humans, by the spinal and the brain.
  • the main and specific function of the central nervous system is the implementation of simple and complex highly differentiated reflective reactions, called reflexes.
  • the lower and middle sections of the central nervous system - the spinal cord, medulla oblongata, midbrain, diencephalon and cerebellum regulate the activity of individual organs and systems of a highly developed organism, carry out communication and interaction between them, ensure the unity of the body and the integrity of its activity.
  • the highest part of the central nervous system - the cerebral cortex and the nearest subcortical formations - mainly regulates the relationship and relationships of the body as a whole with the environment.
  • An effector is a chemical substance (small molecule, lipid, macromolecule, nucleotide, inorganic ion, peptide, protein, etc.) that can interact with receptors or binding sites of a biological target, which leads to the inhibition or activation or specific modification of the functions of a biomolecule.
  • Alkyl means an aliphatic hydrocarbon linear or branched group with 1-12 carbon atoms in the chain. Branched means that the alkyl chain has one or more "lower alkyl" substituents.
  • the term lower alkyl means a straight or branched chain alkyl group containing from 1 to 7 carbon atoms, examples of which are methyl, ethyl, isopropyl, butyl, sec-butyl, tert-butyl and the like.
  • alkenyl and alkynyl have similar meanings, but their hydrocarbon chains contain double and triple carbon-carbon bonds, respectively.
  • Alkoxy means an alkyl-O- group in which alkyl is defined in this section.
  • alkyloxy groups are methoxy, ethoxy, n-propoxy, iso-propoxy.
  • Annelated cycle means a bi- or poly-cyclic system in which the annelated cycle and the cycle with which it is “anealed” have at least two common atoms.
  • Aralkyl means an alkyl group substituted with one or more aryl groups.
  • aralkyl groups are benzyl, 2,2-diphenylethyl or phenethyl.
  • Aryl means one or more 5- or 6-membered aromatic rings.
  • Apyl may be a condensed polycycle, for example, as naphthalene, or non-condensed, for example, as biphenyl.
  • Substituted aryl has one or more substituents.
  • Aromatic cycle means a planar cyclic system in which all atoms of the cycle participate in the formation of a single conjugation system, which, according to the Hückel rule, includes (4n + 2) ⁇ -electrons (n is a non-negative integer).
  • aromatic cycles are benzene, naphthalene, anthracene, and the like.
  • ⁇ -electrons and p-electrons of heteroatoms participate in the conjugation system; their total number is also equal to (4n + 2).
  • Examples of such cycles are pyridine, thiophene, furan, thiazole and the like.
  • acyl group means a —C (O) R fragment (in which R is H, alkyl, aryl, heterocyclyl, aralkyl and the like).
  • R is H, alkyl, aryl, heterocyclyl, aralkyl and the like.
  • acyl groups include formyl, acetyl, benzoyl, phenylacetyl and similar groups.
  • Halogen means an atom of fluorine, chlorine, bromine or iodine.
  • Heterocycle means one or more optionally fully saturated or aromatic 5-, 6- or 7-membered rings containing at least one heteroatom, for example, sulfur, oxygen or nitrogen.
  • the heterocycle may be a condensed polycycle, for example, as benzimidazole, benzoxazole, benzthiazole, indole, quinoline or non-condensed, for example, as pyrimidine, bipyridine.
  • Azaheterocycle means a heterocycle comprising at least one nitrogen atom, for example, indole, pyridine, pyrimidine, triazine, morpholine, piperidine, thiomorpholine, piperazine, homopiperazine, imidazole, thiazole, imidazoline, indoline, benzimazolezole .
  • Optical isomers are spatial isomers, the molecules of which are related to each other as an object and an incompatible mirror image (like the left and right hands). Two such stereoisomers are called enantiomers, and each of these structures is chiral. The existence of two enantiomers in this case is due to a carbon atom having four different substituents.
  • SUBSTITUTE SHEET (RULE 26) an asymmetric carbon atom is called a stereocenter or chiral center. A mixture of equal amounts of both enantiomers is called racemic.
  • Z is optionally substituted - (CH 2 ) m -, - (CH 2 ) m NH—, - (CH 2 ) m O— or - (CH 2 ) m S—; m can take values 2, 3 and 4;
  • Ar is optionally substituted aryl or hetaryl, for example, such as naphthalene, pyridine, piperidine, indole, benzimidazole, benzoxazole, benzothiazole, indazole, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
  • Rl is H, optionally substituted alkyl, optionally substituted alkoxy, halogen, OH, CF3, CN, CFZO, optionally substituted amino group, acyl group, optionally substituted aryl or hetaryl, alkenyl, alkynyl, aralkyl, alkoxycarbonyl, sulfonyl, sulfinyl, optionally substituted amino-sulfonyl and the like; Rl also means the possibility of the presence of an annelated cycle, for example, formed by fragments such as methylenedioxy, ethylenedioxy, etc .;
  • R2 represents H, methyl, optionally substituted alkyl or benzyl
  • Q is optionally substituted —CH 2 CH 2 - or —CH 2 CH 2 O—;
  • Alkl is methyl or ethyl
  • ArI is optionally substituted phenyl or a 6-membered azaheterocycle, for example, such as phenyl, pyridine, piperidine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
  • Rl and R2 are as defined above.
  • stereoisomerically pure (si ⁇ jon isomer) subgroups of the substances represented by general formulas Ll.1, 1.1.2, 1.2.1 are preferred , 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2:
  • ArI, Rl, R2, and Q are as defined above.
  • SUBSTITUTE SHEET 180. 2-ethyl-3,7,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
  • the next object constituting the present invention is the compounds of the general formula I proposed by the authors, having physiological activity, namely, neuroprotective properties and the ability to effectively stimulate cognitive functions, which allows them to be used as medicinal substances, compositions and preparations for humans and warm-blooded animals intended for the treatment of neurodegenerative diseases.
  • the next object that makes up the present invention are physiologically active substances of the General formula I, showing the properties of antagonists of serotonin receptors 5-HT6.
  • the next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of 5-HT7 antagonists of serotonin receptors.
  • the next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of BChE butyrylcholinesterase inhibitors.
  • the next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of MPTP mitochondrial pore effectors.
  • the next preferred object constituting the present invention are physiologically active substances of General formula I, at the same time
  • SUBSTITUTE SHEET (RULE 26) exhibiting the properties of serotonin receptor antagonists and butyryl cholinesterase BChE inhibitors.
  • the next preferred object constituting the present invention are physiologically active substances of the general formula I, simultaneously exhibiting the properties of antagonists of serotonin receptors and effectors of mitochondrial pores MPTP.
  • the next most preferred object constituting the present invention are physiologically active substances of the general formula I, which simultaneously exhibit the properties of serotonin receptor antagonists, BChE butyrylcholinesterase inhibitors and MPTP mitochondrial pore effectors.
  • the next object constituting this invention are medicinal substances based on compounds of the general formula I for the manufacture of pharmaceutical preparations and pharmaceutical compositions.
  • compositions developed by the authors with neuroprotective properties, as well as the ability to effectively influence cognitive functions containing the above medicinal substances for use in medicine and veterinary medicine.
  • the proposed compositions as an active substance contain a pharmaceutically effective amount of compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2. 2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
  • the term ((effective amount used in this application, means the use of such an amount of a compound of formula I, which in combination with its indicators of activity and toxicity should be effective in this dosage form.
  • the object of the present invention are also methods of creating new pharmaceutical compositions containing, as an active substance, one or more compounds represented by formulas 1, 1-1, 1-2, 1-3, I-4, 1-5, 1.1. 1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
  • the methods consist in mixing a physiologically effective amount of the active substance with excipients and / or diluents inert with respect to the substance, followed by tableting, granulation, encapsulation, suspension, dissolution or dilution and placed in a suitable package.
  • a distinctive feature of the methods is the use of compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2 as the active substance , 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
  • the object of the present invention is also medicines in the form of tablets, gelatine capsules, pills, powders, granules, oral solutions or suspensions, sublingual and buccal forms, aerosols, implants, local, transdermal, subcutaneous, intramuscular, intravenous, intranasal, intraocular or rectal forms, placed in a pharmaceutically acceptable package, and including in its composition a drug substance or pharmaceutical composition containing one or more compounds equations represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2, intended for the treatment and prevention of neurodegenerative diseases, including AD.
  • the object of the present invention is also a method for the treatment and prevention of neurodegenerative diseases of animals and humans whose pathogenesis is associated with dysfunction of the serotonergic and / or cholinergic systems, as well as with dysfunction of the mitochondria.
  • the method consists in the use of new drugs containing as an active substance an effective amount of one or more compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1. 2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
  • the next preferred object constituting the present invention is a method for the treatment and prevention of neurodegenerative diseases in humans or warm-blooded animals, including Alzheimer's and Parkinson's;Huntington's disease (chorea); multiple sclerosis; cerebellar degeneration; amyotrophic lateral sclerosis; dementia with Levy bodies; spinal muscular atrophy; peripheral neuropathy; spongiform encephalitis ' (“bovine rabies”); AIDS-related dementia; multi-infarct dementia; Especially 1 acute dementia; leukoencephalopathy; chronic neurodegenerative diseases; stroke; ischemic, reperfusion, and hypoxic brain damage; epilepsy cerebral ischemia; glaucoma; traumatic brain injury; Down syndrome; encephalomyelitis; meningitis; encephalitis; neuroblastoma; schizophrenia; depression, as well as neuronal damage associated with autoimmune, infectious, oncological and endocrine diseases; and other neurodegenerative processes.
  • neurodegenerative diseases including Alzheimer's and Parkinson
  • the next preferred object constituting the present invention is a method for the treatment and prevention of neurodegenerative processes in humans or warm-blooded animals associated with aging of the body.
  • the next preferred object constituting the present invention is a method of treating and preventing neurodegenerative diseases by administering to a human or warm-blooded animal a drug at a dose of 0.005 to 10.0 mg / kg body weight at least once a day for a period necessary to achieve a therapeutic effect.
  • the next object constituting this invention are compounds of general formula I, which have the property to effectively act on 5-HT6 and / or 5-HT7 serotonin receptors, and / or on BuChE butyrylcholinesterase and / or mitochondria, intended for experimental study of biochemical signal systems and physiological IP vitro and ip vivo processes as ((pharmacological instruments)).
  • the next object that makes up the present invention is a method developed by the authors for the preparation of compounds represented by formula 1.1. According to the present invention, the compounds of formula 1.1 are obtained in accordance with scheme 1.

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Abstract

The present invention relates to novel physiologically active hydrogenated pyrido[4,3-b]indole derivatives which exhibit neuroprotective and cognitive stimulatory activity attributable to the interaction of the aforesaid substances with 5-HT6 and 5-HT7 serotonin receptors, butyrylcholinesterase inhibition and action on the mitochondria. The invention relates to medicinal substances, pharmaceutical compositions having the novel hydrogenated pyrido[4,3-b]indole derivatives as the base thereof and novel drugs which can be used to treat diseases and conditions of the central nervous system of humans and warm-blooded animals. The invention also relates to the use of the aforementioned substances, compositions and preparations in the field of medicine and can be used in the manufacture of neuropharmacological agents for treating neurodegenerative diseases and restoring memory and other cognitive functions lost as a result of disease, time or adverse effects. The invention can also be used to produce novel "molecular pharmacological instruments" which make it possible to study (in vitro and in vivo) the biochemical signalling systems and neurochemical mechanisms of the central nervous system. The group of claimed compounds includes novel hydrogenated pyrido[4,3-b]indole derivatives substituted at positions 1 and/or 3 of the piperidine fragment, in the form of bases or salts thereof with pharmacologically acceptable acids, as well as in the form of individual optical isomers or blends thereof, represented collectively by the general formula I.

Description

Производные гидрированных пиpидo[4,3-b] индолов, фармацевтическая композиция, способы получения и применения  Derivatives of hydrogenated pyrido [4,3-b] indoles, pharmaceutical composition, methods for their preparation and use
Данное изобретение относится к новым физиологически активным производным гидрированных пиpидo[4,3-b]индoлoв, проявляющим нейропротекторную и когнитивно- стимулирующую активности, которые связаны с взаимодействием этих веществ с серотониновыми рецепторами 5-HT6 и 5-HT7, ингибированием бутирилхолинэстеразы и воздействием на митохондрии, в том числе и с одновременным воздействием этих веществ на указанные биомишени. Изобретение относится к лекарственным субстанциям, фармацевтическим композициям, содержащим в качестве лекарственного начала новые производные гидрированных пиpидo[4,3-b]индoлoв, к новым лекарственным средствам, применяемым для лечения болезней и состояний центральной нервной системы (ЦНС) людей и теплокровных животных. Изобретение также относится к применению указанных субстанций, композиций и препаратов в области медицины и может быть использовано для изготовления нейрофармакологических средств для лечения нейродегенеративных заболеваний, восстановления памяти и других когнитивных функций, утраченных в результате патологии, времени или неблагоприятных воздействий. Изобретение может быть использовано также для создания новых «мoлeкyляpныx фармакологических инструментов)), позволяющих проводить исследования {iп vitrо и iп vivό) биохимических сигнальных систем и нейрохимических механизмов ЦНС. This invention relates to new physiologically active derivatives of hydrogenated pyrido [4,3-b] indoles, which exhibit neuroprotective and cognitively stimulating activities that are associated with the interaction of these substances with 5-HT 6 and 5-HT 7 serotonin receptors, butyrylcholinesterase inhibition and exposure on mitochondria, including with the simultaneous effect of these substances on these biological targets. The invention relates to medicinal substances, pharmaceutical compositions containing new derivatives of hydrogenated pyrido [4,3-b] indoles as a drug principle, to new drugs used to treat diseases and conditions of the central nervous system (CNS) of humans and warm-blooded animals. The invention also relates to the use of these substances, compositions and preparations in the field of medicine and can be used for the manufacture of neuropharmacological agents for the treatment of neurodegenerative diseases, memory restoration and other cognitive functions lost as a result of pathology, time or adverse effects. The invention can also be used to create new "molecular pharmacological tools)), allowing research (ip vitro and ip vivό) of biochemical signal systems and neurochemical mechanisms of the central nervous system.
Предпосылки создания изобретения  BACKGROUND OF THE INVENTION
Деменция в настоящее время является самой серьезной медицинской проблемой пожилого возраста, которая проявляется у 4% населения в возрасте 65 лет и по крайней мере у 35% населения в возрасте 85 лет [Fеrri СР., Prince M., Вгаупе С. Вrоdаtу H., Fгаtigliопi L., Ganguli M., HaIl К., Наsеgаwа К., Hendrie H., Huang Y., Jоrm А., Маthеrs С, Мепеzеs P. R., Rimmег E., Sсаufса M; Аlzhеimеr's Disеаsе Iпtеrпаtiопаl. Glоbаl рrеvаlепсе оf dеmепtiа: а Dеlрhi сопsепsus studу. Lапсеt. 2005; Збб:2\ \2—2\ 17].. В 2005 году в мире насчитывалось более 24 миллионов больных, страдающих от деменции, в связи с увеличением продолжительности жизни их число стремительно растет и, предполагается, достигнет 80 миллионов в 2040 году [Fеrri СР., Prince M., Вгаупе С. Вrоdаtу H., Fгаtigliопi L., Ganguli M., HaIl К., Наsеgаwа К., Hendrie H., Huang Y., Jоrm А., Маthеrs С, Мепеzеs P. R., Rimmег E., Sсаufса M; Аlzhеimеr's Disеаsе Iпtеrпаtiопаl. Glоbаl рrеvаlепсе оf dеmепtiа: а Dеlрhi сопsепsus studу. Lапсеt. 2005; 566:2112-2117]. Наиболее распространенной формой деменции является болезнь Альцгеймера (БА - около 60% всех случаев), представляющая собой прогрессирующее необратимое нейродегенеративное заболевание  Dementia is currently the most serious medical problem of the elderly, which occurs in 4% of the population aged 65 and at least 35% of the population aged 85 [Ferri CP., Prince M., Waupe S. Wrodatu H., Ftigliopi L., Ganguli M., HaIl K., Hasegawa K., Hendrie H., Huang Y., Jorm A., Mathers C, Mepeses PR, Rimmeg E., Saufsa M; Alzheimer Disase Ipterpatiopl. Globalrevalepse of demetia: and Delphi sceptsus studu. Lapett. 2005; Zbb: 2 \\ 2-2 \ 17] .. In 2005, there were more than 24 million patients suffering from dementia in the world, due to the increase in life expectancy, their number is growing rapidly and is expected to reach 80 million in 2040 [Ferri CP., Prince M., Vgaupe S. Wrodatu H., Fatigliopi L., Ganguli M., HaIl K., Nasegawa K., Hendrie H., Huang Y., Jorm A., Mathers C, Mepes PR, Rimmeg E ., Saufsa M; Alzheimer Disase Ipterpatiopl. Globalrevalepse of demetia: and Delphi sceptsus studu. Lapett. 2005; 566: 2112-2117]. The most common form of dementia is Alzheimer's disease (AD - about 60% of all cases), which is a progressive irreversible neurodegenerative disease
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) с недостаточно изученным патогенезом. По мере прогрессирующей гибели нейронов наиболее яркими клиническими проявлениями БА становятся потеря памяти и нарастающие когнтивные затруднения. В качестве дополнительных симптомов наблюдаются неспособность придерживаться привычного образа жизни и поведенческие расстройства, также усиливающиеся по мере развития заболевания [Вгооkmеуеr R., Jоhпsоп E., Zеiglеr-Grаhаm К., Агrighi Н.М. Fоrесаstiпg thе glоbаl burdеп оf Аlzhеimег's disеаsе. Аlzhеiтеr 's Dетепt. 2007; 5:186 -191]. БА в настоящее время практически не имеет эффективных средств лечения. Разработка таких средств интенсивно ведется на протяжении многих лет, однако до сих пор основным направлением поиска остается попытка фармакологической коррекции холинергического дефицита [Мауеuх R., Sano M. Тгеаtmепt оf Аlzhаimеr's disеаsе. N. Епgl. J. Меd. 1999; 341 : 1670-1679], приведшая к созданию ряда препаратов на основе ингибиторов ацетилхолинэстеразы (Такрин, Амиридин, Арисепт и т.п.), имеющих однако весьма ограниченную клиническую применимость. Широко применяется сейчас также антагонист NMDA рецепторов Мемантин, который приводит к кратковременному улучшению когнитивных функций, однако практически не предотвращает прогрессию Б А [Frапсis P. T. Glutаmаtегgiс арргоасhеs tо thе trеаtmепt оf соgпitivе апd bеhаviоurаl sуmрtоms оf Аlzhеimеr's disеаsе. Nеиrоdеgепеr. Dis. 2008; 5(5-4) :241-243]. SUBSTITUTE SHEET (RULE 26) with insufficiently studied pathogenesis. With the progressive death of neurons, the most striking clinical manifestations of AD are memory loss and increasing cognitive difficulties. As additional symptoms, there is an inability to adhere to a habitual lifestyle and behavioral disorders, which also increase with the development of the disease [Vgokomueuer R., Johnsop E., Zeigler-Graham K., Agrighi N.M. Forcesstiпgее global burde оf Аlzheimeg's disеasе. Algerite's Dept. 2007; 5: 186 -191]. AD currently has virtually no effective treatment. The development of such drugs has been intensively carried out for many years, but so far the main focus of the search remains an attempt at pharmacological correction of cholinergic deficiency [Maueuh R., Sano M. Tgeatmept of Alzhaimer diséase. N. Epgl. J. Med. 1999; 341: 1670-1679], which led to the creation of a number of drugs based on acetylcholinesterase inhibitors (Takrin, Amiridin, Arisept, etc.), which however have very limited clinical applicability. Nowadays, the NMDA receptor antagonist Memantine is also widely used, which leads to a short-term improvement in cognitive functions, but practically does not prevent the progression of B A [Frapsis PT Glutamategos argotaschetoteptompot ofpot apm béhaviulélémsempém. Neurodegepera. Dis. 2008; 5 (5-4): 241-243].
В этой связи поиск высоко-эффективных средств лечения и ранней диагностики БА с принципиально новым механизмом действия, в особенности препаратов, блокирующих или тормозящих развитие нейродегенеративных процессов (disеаsе-mоdifуiпg thегарiеs [Sаllоwау S., Мiпtzеr J., Wеiпеr M.F., Сummiпgs J.L. Disеаsе-mоdifуiпg thегарiеs iп Аlzhеimег's disеаsе. Аlzhеiтеr's Dетепtiа. 2008; 4:65-79]), становится все более актуальной задачей [Jеlliпgег К. А. Аlzhеimеr 100 - highlights iп thе histоrу оf Аlzhеimеr rеsеаrсh. J Nеиrаl Тrапsт. 2006; 7/5(7/,): 1603-1623]. В настоящее время поиск таких средств ведется весьма интенсивно и в рамках различных подходов.  In this regard, the search for highly effective treatment and early diagnosis of asthma with a fundamentally new mechanism of action, in particular drugs that block or inhibit the development of neurodegenerative processes (diséasémodifuipg tegariès [Sallowau S., Miptzer J., Weeper MF, Summpgs JL Disap modifеgе tegariеs ip Alzheimeg's disеce. Аlzheiter's Detetia. 2008; 4: 65-79]), is becoming an increasingly urgent task [Jellipgeg K. A. Alzheimer 100 - highlights ip tehistoru оf Alzheimer res. J Neural Trast. 2006; 7/5 (7 /,): 1603-1623]. Currently, the search for such funds is very intensive and in the framework of various approaches.
Один из наиболее перспективных подходов в лечении БА и других нейродегенеративных заболеваний основан на использовании высокоэффективных антагонистов серотониновых 5-HT6 рецепторов [Ноlепz J., Раuwеls P.J., Diаz J.L., Меrсе R., Codony X., Buschmann H. Меdiсiпаl сhеmistrу strаtеgiеs tо 5-HT6 rесерtоr ligапds аs роtепtiаl соgпitivе епhапсеrs апd апtiоbеsitу аgепts. Drиg Disс. Тоdау. 2006; /7:283-299]. Эти рецепторы у млекопитающих находятся исключительно в ЦНС, причем главным образом в участках головного мозга, ответственных за обучение и память [Gе'rаrd С, Маrtгеs M.- P., Lеfе'vrе К., Мiquеl M. -С, Vеrgе' D., Lanfumey L., Dоuсеt E., Hamon M., El Меstikаwу S. Immuпо-lосаlisаtiоп оf serotonin 5-HT6 rесерtоr-likе mаtеriаl iп thе rаt сепtrаl пеrvоus sуstеm. One of the most promising approaches in the treatment of AD and other neurodegenerative diseases is based on the use of highly effective antagonists of serotonin 5-HT 6 receptors [Holepz J., Powels PJ, Diaz JL, Merce R., Codony X., Buschmann H. Medicinal chemotherapy -HT 6 Resource Ligapds As Potential Companion Appts Apothec Agents. Drig Dis. Todau. 2006; / 7: 283-299]. These receptors in mammals are found exclusively in the central nervous system, and mainly in the areas of the brain responsible for learning and memory [Ge'rard C, Martes M.-P., Leffe K., Miquel M.-C, Verge D ., Lanfumey L., Doucet E., Hamon M., El Mestikawu S. Immu-losalisatiop of serotonin 5-HT 6 test-lika material іp thе rаt septrаl pervus sustеm.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Вrаiп Rеsеаrсh. 1997; 746:207-219]. Показано также, что 5-HT6 рецепторы являются модуляторами нескольких нейромедиаторных систем, включая холинэргическую, норадренэргическую, глутаматэргическую и допаминэргическую [Dаwsоп L. А., Nguуеп H.Q., Li P. Тhе 5-HT(6) rесерtоr апtаgопist SB-271046 sеlесtivеlу епhапсеs ехсitаtоrу пеuгоtrапsmissiоп iп thе rаt frопtаl соrtех апd hiрросаmрus. Nеиrорsусhорhаrтасоlоgу. 2001; 25:662-668]. Эти системы играют важную роль в нормальных когнитивных процессах, их дисфункция наблюдается при нейродегенерации, что указывает на исключительное значение 5-HT6 рецепторов в процессах формирования и восстановления памяти. В большом числе современных работ показано, что блокирование 5-HT6 рецепторов приводит к значительному усилению консолидации памяти в различным животных моделях обучения-запоминания-воспроизведения [Кiпg M.V., Wооllеу M.L., Торhаm I.A., Slеight A.J., Магsdеп C.A., Fопе К.С. 5-HT6 rесерtоr -апtаgопists rеvеrsе dеlау-dерепdепt dеfiсits iп поvеl оbjесt disсrimiпаtiоп bу епhапсiпg сопsоlidаtiоп ап еffесt sепsitivе tо NMDA rесерtоr апtаgопism. Nеurорhаrmасоlоgу 2004; 47: 195-204]. SUBSTITUTE SHEET (RULE 26) Vraip Research. 1997; 746: 207-219]. It has also been shown that 5-HT 6 receptors are modulators of several neurotransmitter systems, including cholinergic, noradrenergic, glutamatergic and dopaminergic [Dawsop L. A., Nguyep HQ, Li P. The 5-HT (6) receptor drug eksitatoru pegotrapsmissiop ip tеrrat froptal sortex apd hirrosamrus. Neurosushorhortasologu. 2001; 25: 662-668]. These systems play an important role in normal cognitive processes, their dysfunction is observed during neurodegeneration, which indicates the exceptional importance of 5-HT 6 receptors in the processes of memory formation and recovery. In a large number of modern works, it has been shown that blocking 5-HT 6 receptors leads to a significant increase in memory consolidation in various animal models of learning-memorization-reproduction [Кіпg MV, Woоlleu ML, Тхам IA, Slight AJ, Magdep CA, Fope K.S. 5-HT6 receptor-apagopists reverse dela-defept defits іp pobel waited for disсrimiпtiop бu ehsapsipg ssolidіtiop ap effest sepsitiva te NMDA reserptism. Neuroharmacology 2004; 47: 195-204].
Серотонинэргическая система представляется особенно перспективной как совокупность биомишеней для лечения БА, поскольку она вовлечена не только в когнитивные функции, но и в процессы формирования депрессии, психозов и агрессии - то есть в проявление дополнительных симптомов БА [Uрtоп N., Сhuапg Т., Hunter A., Virlеу D. 5-HT6 Rесерtоr Апtаgопists аs Nоvеl Соgпitivе Епhапсiпg Аgепts fоr Аlzhеimеr's Disеаsе. Nеиrоthеrареиtiсs. 2008; 5:458^469]. В этом плане многообещающим «дoпoлнeниeм» к 5-HT6 рецепторам в качестве биомишени являются серотониновые 5-HT7 рецепторы, антагонисты которых в настоящее время рассматриваются как возможные антидепрессанты [5-HT7, Nеurоgепеsis апd апtidерrеssапts: а рrоmisiпg thеrареutiс ахis fоr trеаtiпg dерrеssiоп. Сliпiсаl апd Ехреήтепtаl Рhаrтасоlоgу апd Рhуsiоlоgу. 2007; 34: 546-551]. Таким образом, эффекторы серотонинэргической системы могут проявлять когнитивно-стимулирующие, антидепрессантные и нейролептические свойства The serotonergic system seems to be especially promising as a set of bi-targets for the treatment of AD, since it is involved not only in cognitive functions, but also in the formation of depression, psychosis and aggression - that is, in the manifestation of additional symptoms of AD [Utop N., Khuapg T., Hunter A ., Virleu D. 5-HT6 Resource Pharmaceuticals as Novell Consumer Health Agents for Alzheimer's Disase. Neurothetherareitis. 2008; 5: 458 ^ 469]. In this regard, the serotonin 5-HT 7 receptors, the antagonists of which are currently considered as possible antidepressants [5-HT 7 , drug therapy, and drug therapy, are the promising additions to 5-HT 6 receptors as biotarriers. . Slipal apd Exhrapetal Rhartasolog apd Rhusiologu. 2007; 34: 546-551]. Thus, serotonergic system effectors can exhibit cognitively stimulating, antidepressant, and antipsychotic properties.
Другой перспективный подход в лечении БА основан на использовании высокоэффективных и селективных ингибиторов бутирилхолинэстеразы BChE [Вurtоп А. Inhibition of butyrylcholinesterase could ease AD. Lапсеt Nеиrоl. 2006; 5(1): 27]. В отличие от здорового мозга, где основным ферментом холинэргической системы является ацетилхолинэстераза AChE, в мозгу больных БА прогрессивно возрастает содержание и активность BChE, в то время как активность AChE резко уменьшается. [Grеigd N., Lаhiri E., Аmbаmurti К. Butyrylcholinesterase : An Imроrtапt Nеw Таrgеt iп Аlzhеimеr's Disеаsе Тhеrару. Iпtеrп. Рsусhоgеriаtriсs. 2002; 14(1): 77-91]. Показано, что содержание BChE в амилоидных бляшках у больных БА значительно более высокое, чем содержание этого  Another promising approach in the treatment of AD is based on the use of highly effective and selective BChE butyrylcholinesterase inhibitors [Wurtop A. Inhibition of butyrylcholinesterase could ease AD. Lapet Neyrol. 2006; 5 (1): 27]. Unlike a healthy brain, where acetylcholinesterase AChE is the main enzyme of the cholinergic system, the content and activity of BChE in the brain of AD patients progressively increases, while AChE activity sharply decreases. [Greigd N., Lahiri E., Ambamurti K. Butyrylcholinesterase: An Imroptap New Target ip Alzheimer Disase Thearu. Ipterp. PSUCHOGERIATRIS. 2002; 14 (1): 77-91]. It was shown that the content of BChE in amyloid plaques in patients with asthma is significantly higher than the content of this
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) фермента в сенильных бляшках не подверженного деменции мозга. Более того, присутствие BChE вместе с бета-амилоидом в культуре нейронов значительно увеличивает нейротоксичность последнего [Саrгеiгаs M. С, Магсо J. L. Rесепt Арргоасhеs tо Nоvеl Апti-Аlzhеimег Тhеrару. Сиrrепt Рhаrтасеиtiсаl Dеsigп. 2004; 10: 3167-3175]. Кроме того, в процессах нейронального роста существенное значение имеет нехолинэргические функции BChE, ингибирование которых стимулирует нейрогенезис [Масk А., Rоbitzki А. Тhе kеу rоlе оf butугуlсhоliпеstегаsе duriпg пеuгоgепеsis апd пеuгаl disоrdеrs: ап апtisепsе- 5'butyrylcholinesterase-DNA studу. Рrоg. Nеиrоbiоl. 2000; 60(6): 607-628]. Таким образом эффективные ингибиторы BChE могут проявлять свойства как когнитивных стимуляторов, повышая уровень ацетилхолина, так и нейропротекторов, понижая токсичность бета-амилоида и стимулируя нейрогенезис. SUBSTITUTE SHEET (RULE 26) enzyme in senile plaques not affected by dementia of the brain. Moreover, the presence of BChE together with beta-amyloid in the culture of neurons significantly increases the neurotoxicity of the latter [Сargeigas M. S, Magso JL Resept Arrgoashes to Novel Apti-Alzhemeg Thearu. Syrup Rhartaseitisal Desigp. 2004; 10: 3167-3175]. In addition, in the processes of neuronal growth, the non-cholinergic functions of BChE are essential, the inhibition of which stimulates neurogenesis. Rog. Neurobiol. 2000; 60 (6): 607-628]. Thus, effective BChE inhibitors can exhibit the properties of both cognitive stimulants, increasing the level of acetylcholine and neuroprotectors, lowering the toxicity of beta-amyloid and stimulating neurogenesis.
Новый перспективный подход в лечении нейродегенеративных заболеваний заключается в использовании протекторов нейрональных митохондрий [Jоhп Xi Сhепа J.X., Yапb S.D. Аmуlоid-β-Iпduсеd Мitосhопdriаl Dуsfuпсtiоп. J Аlzhеiтеr 's Dis. 2007; 12 : 177-184]. Митохондрии не только энергетически обеспечивают клетки, но и определяют их судьбу. В частности, окислительный стресс, являющийся составной частью нейродегенеративного процесса, сопровождается избыточным входом в митохондрии ионов кальция и сольволизом АТФ, что приводит к образованию неспецифических митохондриальных пор (mitосhопdriаl реrmеаbilitу trапsitiоп роге - MPTP). Открытие митохондриальных пор сопровождается неконтролируемыми процессами окислительного фосфорилирования и деструкции вторичных мессенджеров, что приводит к гибели нейронов. Таким образом вещества, блокирующие открытие MPTP пор, представляют большой интерес как нейропротекторы [Jаvаdоs S., Каrmаzуп M., Еsсоbаlеs N. Mitосhопdriаl реrmеаbilitу trапsitiоп роге орепiпg аs а рrоmisiпg thегареutiс tаrgеt iп саrdiас disеаsеs. J. Рhагm. Ехр. Тhеr. 2009; Juп 9. {Ерub аhеаd оf рriпt}].  A new promising approach in the treatment of neurodegenerative diseases is the use of protectors of neuronal mitochondria [John Xi Chepa J.X., Yapb S.D. Amuloid-β-Ipduced Mitoshopdrial Dusfuptiop. J Algerite's Dis. 2007; 12: 177-184]. Mitochondria not only energetically provide cells, but also determine their fate. In particular, oxidative stress, which is an integral part of the neurodegenerative process, is accompanied by excessive entry of calcium ions into the mitochondria and ATP solvolysis, which leads to the formation of nonspecific mitochondrial pores (mitochondrial receptor trumpsi horn MPTP). The opening of mitochondrial pores is accompanied by uncontrolled processes of oxidative phosphorylation and destruction of secondary messengers, which leads to the death of neurons. Thus, substances that block the opening of MPTP pores are of great interest as neuroprotectors [Javados S., Karmazup M., Escobales N. Mitosopriel rhempabilit and apricotasperitic disgeset. J. Phagm. Exp That. 2009; Jup 9. {Еруб ахед оf ррипt}].
В целом, процессы, вызывающие гибель - нейронов, крайне сложны и многообразны. В этих процессах участвуют множество потенциальных биомишеней (например, белки, управляющие апоптозом, мишени амилоидного каскада и других протеинопатий, эффекторы окислительного стресса, воспалительных процессов, эксайтотоксичности и др. [Lаhiri D. К., Fаrlоw M.R., Sаmbаmurti К., Grеig N. H., Giасоbiпi E., Schneider L. S. А сritiсаl апаlуsis оf пеw mоlесulаr tаrgеts апd strаtеgiеs fоr dгug dеvеlорmепts iп Аlzhеimеr's disеаsе. Сиrr. Dгug Tаrgеts. 2003; 4: 97-112]). Неудивительно, что разработка терапевтических методов и получение нейропротекторов, позволивших бы предотвратить развитие заболевания, является весьма непростой задачей. Для подобного рода сложных случаев, когда необходим одновременный анализ множества  In general, the processes that cause the death of neurons are extremely complex and diverse. Many potential target targets are involved in these processes (for example, proteins that control apoptosis, targets of the amyloid cascade and other proteinopathies, effectors of oxidative stress, inflammatory processes, excitotoxicity, etc. [Lahiri D. K., Farow MR, Sambamurti K., Green NH, Giasobiipi E., Schneider LS A critical apalysis of the first molsulart targets apd strägeties for dgug devémeptes ip Algerimé disés. Cirr. Dgug Target1-1.2); 4). 4). 4). 4). It is not surprising that the development of therapeutic methods and the production of neuroprotectors that would prevent the development of the disease is a very difficult task. For this kind of complex cases, when the simultaneous analysis of many
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) лекарственных мишеней (как, например, при рассмотрении этиологии БА) была разработана новая концепция поиска лекарственных препаратов. В отличие от классической схемы, подразумевающей избирательное взаимодействие активного соединения с одной биомишенью, в предложенной концепции многофункционального дизайна препаратов учитываются одновременные взаимодействия со многими биомишенями. [Vап dеr Sсhуf CJ. , Geldenhuys WJ. , Yоudim М.В. Мultifuпсtiопаl пеurорrоtесtivе drugs fог thе trеаtmепt оf соgпitivе апd mоvеmепt imраirеd disоrdеrs, iпсludiпg Аlzhеimег's апd Рагkiпsоп's disеаsеs. Drugs Fиtиrе. 2006; 31: 447-460]. SUBSTITUTE SHEET (RULE 26) drug targets (as, for example, when considering the etiology of AD), a new concept for the search for drugs was developed. Unlike the classical scheme, which implies selective interaction of the active compound with one biological target, the proposed concept of multifunctional drug design takes into account simultaneous interactions with many biological targets. [Vap der Skhuf CJ. Geldenhuys WJ. , Yudim M.V. Multifuptiopal peororotivist drugs og thе treаtmept оf сompitiv аp mоvеmept imrairеd disоrdеrs, ipсludiпg Аlzheimeg's apt Рагкипсоп's disеасеs. Drugs Fitre. 2006; 31: 447-460].
С целью разработки новых высокоэффективных препаратов для лечения нейродегенеративных заболеваний, в частности БА, авторами данного изобретения выполнены широкие скрининговые исследования соединений различных классов, при этом были обнаружены соединения-лидеры, относящиеся к семейству гидрированных пиpидo[4,3-b]индoлoв, затем проводились направленные синтетические модификации обнаруженных структур, и в результате получены серии новых производных указанного семейства, которые сочетают свойства нейропротекторов и когнитивных стимуляторов. В частности, новые соединения являются оригинальными и высокоэффективными антагонистами серотониновых рецепторов 5-HT6 и 5-HT7, ингибиторами бутирилхолинэстеразы и блокаторами митохондриальных пор. In order to develop new highly effective drugs for the treatment of neurodegenerative diseases, in particular, AD, the authors of the present invention carried out extensive screening studies of compounds of various classes, while leading compounds belonging to the hydrogenated pyrido [4,3-b] indole family were discovered, and then conducted directed synthetic modifications of the detected structures, and as a result, a series of new derivatives of the specified family were obtained that combine the properties of neuroprotectors and cognitive stimuli horov. In particular, the new compounds are original and highly effective antagonists of the 5-HT 6 and 5-HT 7 serotonin receptors, butyrylcholinesterase inhibitors and mitochondrial pore blockers.
Полученные вещества ранее не были описаны в литературе.  The resulting substances have not previously been described in the literature.
Авторы также показали возможность использования этих соединений в качестве лекарственных субстанций для фармацевтических композиций и лекарственных препаратов, показали возможность их применения для лечения и предупреждения различных патологических состояний и заболеваний ЦНС.  The authors also showed the possibility of using these compounds as medicinal substances for pharmaceutical compositions and drugs, showed the possibility of their use for the treatment and prevention of various pathological conditions and diseases of the central nervous system.
Ниже приведены определения терминов, которые использованы в описании изобретения.  The following are definitions of terms that are used in the description of the invention.
Антагонист означает лиганд, который связывается с рецепторами определенного типа и не вызывает активного клеточного ответа. Антагонисты препятствуют связыванию агонистов с рецепторами и тем самым блокируют передачу специфического рецепторного сигнала.  Antagonist means a ligand that binds to receptors of a certain type and does not cause an active cellular response. Antagonists inhibit the binding of agonists to receptors and thereby block the transmission of a specific receptor signal.
Деменция (dетепtiά) означает приобретённое слабоумие, стойкое снижение познавательной деятельности с утратой в той- или иной степени ранее усвоенных знаний и практических навыков и затруднением или невозможностью приобретения новых. Деменция обусловлена распадом психических функций, происходящим в результате поражений мозга, например, при старении (сенильная деменция), или в результате нейродегенеративных заболеваний, например, при БА.  Dementia (deteptiά) means acquired dementia, a persistent decline in cognitive activity with the loss to one degree or another of previously acquired knowledge and practical skills and the difficulty or impossibility of acquiring new ones. Dementia is caused by the breakdown of mental functions that occurs as a result of brain damage, for example, during aging (senile dementia), or as a result of neurodegenerative diseases, for example, in AD.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Лекарственное средство (препарат), лекарство (dгug, mеdiсiпе) - вещество (или смесь веществ в виде фармацевтической композиции), предназначенное для восстановления, исправления или изменения физиологических функций у человека и животных, а также для лечения и профилактики болезней, диагностики, анестезии, контрацепции, косметологии и прочего. SUBSTITUTE SHEET (RULE 26) Medicinal product (preparation), medicine (d dug, medisipé) - a substance (or a mixture of substances in the form of a pharmaceutical composition) intended to restore, correct or alter physiological functions in humans and animals, as well as for the treatment and prevention of diseases, diagnosis, anesthesia, contraception, cosmetology and other things.
Лекарственная субстанция (активная субстанция, лекарственное вещество, drug- substапсе) означает физиологически активное вещество синтетического или иного (биотехнологического, растительного, животного, микробного и прочего) происхождения, обладающее фармакологической активностью и являющееся активным началом фармацевтической композиции, используемой для производства и изготовления лекарственного препарата (средства).  Medicinal substance (active substance, medicinal substance, drug substitution) means a physiologically active substance of synthetic or other (biotechnological, plant, animal, microbial and other) origin, having pharmacological activity and is the active principle of the pharmaceutical composition used for the manufacture and manufacture of a medicinal product (facilities).
Митохондрия - органелла, имеющаяся во многих эукариотических клетках и производящая АТФ, используемый в клетке в качестве основного источника химической энергии.  Mitochondria is an organelle found in many eukaryotic cells and producing ATP, used in the cell as the main source of chemical energy.
Нейродегенеративные заболевания означают специфические состояния и заболевания, характеризующиеся повреждением и первичной гибелью популяций нервных клеток в определенных областях центральной нервной системы. Нейродегенеративные заболевания вкючают, но не ограничиваются, болезни Альцгеймера и Паркинсона; болезнь (хорею) Хантингтона; рассеянный склероз; мозжечковую дегенерацию; амиотрофический латеральный склероз; деменцию с тельцами Леви; спинальную мускульную атрофию; периферическую нейропатию; губчатый энцефалит («кopoвьe бeшeнcтвo», Сrеutzfеld- Jаkоb Disеаsе); СПИД-ассоциированную деменцию; мультиинфарктную деменцию; лобно- височную деменцию; лейкоэнцефалопатию (болезнь исчезающей белого вещества); хронические нейродегенеративные заболевания; инсульт; ишемическое, реперфузионное и гипоксическое повреждение мозга; эпилепсию; церебральную ишемию; глаукому; черепно-мозговую травму; синдром Дауна; энцефаломиелит; менингит; энцефалит; нейробластому; шизофрению; депрессию. Кроме того нейродегенеративные заболевания включают патологические состояния и расстройства, развивающиеся при гипоксии, злоупотреблении веществами, вызывающих зависимость, при воздействии нейротоксинов, инфекционных и онкологических заболеваниях головного мозга, а также нейрональные повреждения, ассоциированные с аутоиммунньми и эндокринными заболеваниями; и прочие нейродегенеративные процессы.  Neurodegenerative diseases mean specific conditions and diseases characterized by damage and primary death of populations of nerve cells in certain areas of the central nervous system. Neurodegenerative diseases include, but are not limited to, Alzheimer's and Parkinson's; Huntington's disease (chorea); multiple sclerosis; cerebellar degeneration; amyotrophic lateral sclerosis; dementia with Levy bodies; spinal muscular atrophy; peripheral neuropathy; spongiform encephalitis (“bovine rabies”, Creutzfed-Jacob Disase); AIDS-related dementia; multi-infarct dementia; frontotemporal dementia; leukoencephalopathy (a disease of endangered white matter); chronic neurodegenerative diseases; stroke; ischemic, reperfusion, and hypoxic brain damage; epilepsy cerebral ischemia; glaucoma; traumatic brain injury; Down syndrome; encephalomyelitis; meningitis; encephalitis; neuroblastoma; schizophrenia; Depressed In addition, neurodegenerative diseases include pathological conditions and disorders that develop with hypoxia, substance abuse, when exposed to neurotoxins, infectious and oncological diseases of the brain, as well as neuronal damage associated with autoimmune and endocrine diseases; and other neurodegenerative processes.
Память является свойством центральной нервной системы усваивать из опыта информацию, сохранять ее и использовать при решении возникающих задач.  Memory is a property of the central nervous system to absorb information from experience, save it and use it when solving emerging problems.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Рецепторы представляют собой биологические макромолекулы, расположенные на цитоплазматической мембране клетки или внутриклеточно, способные специфически взаимодействовать с ограниченным набором физиологически активных веществ (лигандов) и трансформировать сигнал об этом взаимодействии в определенный клеточный ответ. SUBSTITUTE SHEET (RULE 26) Receptors are biological macromolecules located on the cytoplasmic membrane of a cell or intracellular, capable of specifically interacting with a limited set of physiologically active substances (ligands) and transforming the signal about this interaction into a specific cellular response.
Сигнальная система (сигнальный каскад, каскад передачи сигнала) означает совокупность взаимосвязанных последовательных и параллельных молекулярных процессов регуляции клеточного метаболизма внешними служащих для нее источником материи и энергии. Молекулярные механизмы передачи (транс дукции) внешних сигналов в клетку подразумевают не только передачу сигналов как таковую", но и весь комплекс событий, с ней сопряженных, в том числе усиление, ослабление и подавление (или выключение) сигналов.  The signal system (signal cascade, signal transmission cascade) means a set of interconnected sequential and parallel molecular processes of regulation of cellular metabolism by external sources of matter and energy that serve as its source. The molecular mechanisms of transmission (transduction) of external signals into the cell mean not only the transmission of signals as such, "but also the whole complex of events associated with it, including amplification, attenuation and suppression (or switching off) of signals.
Соединение-лидер (lеаd, lеаd-соmроuпd) означает соединение с подтвержденной максимальной физиологической активностью, найденное в ряду подобных физиологически активных веществ. Соединение-лидер должено также обладать набором определенных свойств, позволяющих на его основе создать потенциальное лекарство (drug-сапdidаtе). К этим свойствам отноеятся селективность действия, отсутствие токсических эффектов, а также ряд физико-химических характеристик, обеспечивающих его высокую биодоступность (например, соблюдение jiравил Липинского [Liрiпski CA. , Lоmbаrdо F., Dominy B. W., Feeney PJ. Ехрегimепtаl апd соmрutаtiопаl аррrоасhеs tо еstimаtе sоlubilitу апd реrmеаbilitу iп drug disсоvегу апd dеvеlорmепt sеttiпgs. Аdv. Drиg Dеliv. Rеv. 2001; 46(1-3) :3-26]).  Leader compound (lead, lead-comupd) means a compound with confirmed maximum physiological activity, found in a series of similar physiologically active substances. The leader compound must also have a set of certain properties that allow it to create a potential medicine (drug-supplement). These properties include selectivity, the absence of toxic effects, as well as a number of physicochemical characteristics that ensure its high bioavailability (for example, compliance with Lipinsky’s rules [Liripski CA., Lombardo F., Dominy BW, Feeney PJ. salubilit apd remebabilit ip drug dissoveg apd devolormpt sttipgs. Adv. Drig Deliv. 2001; 46 (1-3): 3-26]).
Фармакологически приемлемые соли означают все соли, образованные соединениями (основаниями) и фармакологически приемлемыми кислотами, как неорганическими (например, хлористоводородной, серной, фосфорной и т.д.); так и органическими (например, щавелевой, лимонной, винной, малеиновой, янтарной, метилсерной, п- толуолсульфокислотой и т.д.). Кроме того, фармакологически приемлемые соли могут быть образованы соединениями (кислотами) и фармакологически приемлимыми основаниями, при этом могут быть получены как соли металлов (натрия, калия, лития, кальция, магния), так и соли органических оснований (например, различных аминов, гидроксиалкиламинов, основных аминокислот и т.д.).  Pharmacologically acceptable salts mean all salts formed by compounds (bases) and pharmacologically acceptable acids, as inorganic (for example, hydrochloric, sulfuric, phosphoric, etc.); and organic (for example, oxalic, citric, tartaric, maleic, succinic, methyl sulfuric, p-toluenesulfonic acid, etc.). In addition, pharmacologically acceptable salts can be formed by compounds (acids) and pharmacologically acceptable bases, while metal salts (sodium, potassium, lithium, calcium, magnesium) and salts of organic bases (for example, various amines, hydroxyalkylamines can be obtained) , basic amino acids, etc.).
Фармацевтическая композиция означает композицию, включающую в себя лекарственную субстанцию (или несколько таковых) и, по крайней мере, один из компонентов, выбранных из группы, состоящей из фармацевтически приемлимых и фармакологически совместимых наполнителей, растворителей, разбавителей, носителей,  Pharmaceutical composition means a composition comprising a drug substance (or several thereof) and at least one of the components selected from the group consisting of pharmaceutically acceptable and pharmacologically compatible excipients, solvents, diluents, carriers,
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) вспомогательных, распределяющих и воспринимающих средств, средств доставки, таких как консерванты, стабилизаторы, наполнители, измельчители, увлажнители, эмульгаторы, суспендирующие агенты, загустители, подсластители, отдушки, ароматизаторы, антибактериальные агенты, фунгициды, лубриканты, регуляторы пролонгированной доставки, выбор и соотношение которых зависит от природы и способа назначения и дозировки. SUBSTITUTE SHEET (RULE 26) auxiliary, distributing and perceiving means, means of delivery, such as preservatives, stabilizers, fillers, grinders, moisturizers, emulsifiers, suspending agents, thickeners, sweeteners, perfumes, flavors, antibacterial agents, fungicides, lubricants, prolonged delivery regulators, the choice and ratio of which depends on the nature and method of administration and dosage.
Центральная Нервная Система (ЦНС) означает основную часть нервной системы животных и человека, состоящая из скопления нервных клеток (нейронов) и их отростков, представленной у беспозвоночных системой тесно связанных между собой нервных узлов (ганглиев), а у позвоночных животных и человека - спинным и головным мозгом. Главная и специфическая функция ЦНС заключается в осуществлении простых и сложных высокодифференцированных отражательных реакций, получивших название рефлексов. У высших животных и человека низшие и средние отделы ЦНС - спинной мозг, продолговатый мозг, средний мозг, промежуточный мозг и мозжечок - регулируют деятельность отдельных органов и систем высокоразвитого организма, осуществляют связь и взаимодействие между ними, обеспечивают единство организма и целостность его деятельности. Высший отдел ЦНС - кора больших полушарий головного мозга и ближайшие подкорковые образования - в основном регулирует связь и взаимоотношения организма как единого целого с окружающей средой.  The Central Nervous System (CNS) means the main part of the nervous system of animals and humans, consisting of an accumulation of nerve cells (neurons) and their processes, represented in invertebrates by a system of closely connected nerve nodes (ganglia), and in vertebrates and humans, by the spinal and the brain. The main and specific function of the central nervous system is the implementation of simple and complex highly differentiated reflective reactions, called reflexes. In higher animals and humans, the lower and middle sections of the central nervous system - the spinal cord, medulla oblongata, midbrain, diencephalon and cerebellum - regulate the activity of individual organs and systems of a highly developed organism, carry out communication and interaction between them, ensure the unity of the body and the integrity of its activity. The highest part of the central nervous system - the cerebral cortex and the nearest subcortical formations - mainly regulates the relationship and relationships of the body as a whole with the environment.
Эффектор представляет собой химическое вещество (небольшая молекула, липид, макромолекула, нуклеотид, неорганический ион, пептид, белок и прочее), способное взаимодействовать с рецепторами или местами (sitе) связывания биомишени, что приводит к ингибированию или активации или специфической модификации функций биомолекулы.  An effector is a chemical substance (small molecule, lipid, macromolecule, nucleotide, inorganic ion, peptide, protein, etc.) that can interact with receptors or binding sites of a biological target, which leads to the inhibition or activation or specific modification of the functions of a biomolecule.
Химические термины  Chemical terms
Алкил означает алифатическую углеводородную линейную или разветвленную группу с 1-12 атомами углерода в цепи. Разветвленная означает, что алкильная цепь имеет один или несколько «низшиx aлкильныx» заместителей. Термин низший алкил означает алкильную группу с прямой или разветвленной цепью, содержащую от 1 до 7 атомов углерода, примерами которой являются метил, этил, изопропил, бутил, втор-бутил, трет- бутил и аналогичные. Аналогичные значения-имеют термины алкенил и алкинил, однако в их углеводородных цепях содержится соответственно двойная и тройная углерод- углеродная связи.  Alkyl means an aliphatic hydrocarbon linear or branched group with 1-12 carbon atoms in the chain. Branched means that the alkyl chain has one or more "lower alkyl" substituents. The term lower alkyl means a straight or branched chain alkyl group containing from 1 to 7 carbon atoms, examples of which are methyl, ethyl, isopropyl, butyl, sec-butyl, tert-butyl and the like. The terms alkenyl and alkynyl have similar meanings, but their hydrocarbon chains contain double and triple carbon-carbon bonds, respectively.
Алкокси означает алкил-О- группу, в которой алкил определен в данном разделе. Примерами алкилокси групп являются метокси, этокси, н-пропокси, изо-пропокси.  Alkoxy means an alkyl-O- group in which alkyl is defined in this section. Examples of alkyloxy groups are methoxy, ethoxy, n-propoxy, iso-propoxy.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Аннелированный цикл (конденсированный цикл) означает би- или поли-циклическую систему, в которой аннелированный цикл и цикл, с которым он «aнeлиpoвaн», имеют как минимум два общих атома. SUBSTITUTE SHEET (RULE 26) Annelated cycle (condensed cycle) means a bi- or poly-cyclic system in which the annelated cycle and the cycle with which it is “anealed” have at least two common atoms.
Аралкил означает алкильную группу замещенную одним или несколькими арильными группами. Примерами аралкильных групп являются бензил, 2,2-дифeнилэтил или фенетил.  Aralkyl means an alkyl group substituted with one or more aryl groups. Examples of aralkyl groups are benzyl, 2,2-diphenylethyl or phenethyl.
Арил означает один или более 5- или 6-члeнныx ароматических циклов. «Apил» может быть конденсированным полициклом, например, как нафталин или неконденсированным, например, как бифенил. Замещенный арил имеет один или несколько заместителей.  Aryl means one or more 5- or 6-membered aromatic rings. Apyl may be a condensed polycycle, for example, as naphthalene, or non-condensed, for example, as biphenyl. Substituted aryl has one or more substituents.
Ароматический цикл означает планарную циклическую систему, в которой все атомы цикла участвуют в образовании единой системы сопряжения, включающей, согласно правилу Хюккеля, (4n + 2) π-электронов (п - целое неотрицательное число). Примерами ароматических циклов являются бензол, нафталин, антрацен и т.п. В случае гетероароматических циклов в системе- сопряжения участвуют π-электроны и р- электроны гетероатомов, их суммарное число также равняется (4n + 2). Примерами таких циклов являются пиридин, тиофен, фуран, тиазол и т.п.т Aromatic cycle means a planar cyclic system in which all atoms of the cycle participate in the formation of a single conjugation system, which, according to the Hückel rule, includes (4n + 2) π-electrons (n is a non-negative integer). Examples of aromatic cycles are benzene, naphthalene, anthracene, and the like. In the case of heteroaromatic rings, π-electrons and p-electrons of heteroatoms participate in the conjugation system; their total number is also equal to (4n + 2). Examples of such cycles are pyridine, thiophene, furan, thiazole and the like. t
Ацильная группа означает фрагмент -C(O)R (в которой R имеет значения H, алкил, арил, гетероциклил, аралкил и подобные). Примеры ацильных групп включают формильную, ацетильную, бензоильную, фенилацетильную и аналогичные группы.  An acyl group means a —C (O) R fragment (in which R is H, alkyl, aryl, heterocyclyl, aralkyl and the like). Examples of acyl groups include formyl, acetyl, benzoyl, phenylacetyl and similar groups.
Галоген означает атом фтора, хлора, брома или иода. Halogen means an atom of fluorine, chlorine, bromine or iodine.
Гетероцикл означает один или несколько необязательно полностью насыщенных или ароматических 5-, 6- или 7-члeнныx циклов, содержащих по крайней мере один гетероатом, напримр, серу, кислород или азот. Гетероцикл может быть конденсированным полициклом, например, как бензимидазол, бензоксазол, бензтиазол, индол, хинолин или неконденсированным, например, как пиримидин, бипиридин. Азагетероцикл означает гетероцикл, включающий, по крайней мере, один атом азота, например, как индол, пиридин, пиримидин, триазин, морфолин, пиперидин, тиоморфолин, пиперазин, гомопиперазин, имидазол, тиазол, имидазолин, индолин, бензимимдазол, бензоксазол и т.п.  Heterocycle means one or more optionally fully saturated or aromatic 5-, 6- or 7-membered rings containing at least one heteroatom, for example, sulfur, oxygen or nitrogen. The heterocycle may be a condensed polycycle, for example, as benzimidazole, benzoxazole, benzthiazole, indole, quinoline or non-condensed, for example, as pyrimidine, bipyridine. Azaheterocycle means a heterocycle comprising at least one nitrogen atom, for example, indole, pyridine, pyrimidine, triazine, morpholine, piperidine, thiomorpholine, piperazine, homopiperazine, imidazole, thiazole, imidazoline, indoline, benzimazolezole .
Оптические изомеры (стереоизомеры) - пространственные изомеры, молекулы которых относятся между собой как предмет и несовместимое с ним зеркальное изображение (как левая и правая руки). Два таких стереоизомера называются энантиомерами, и каждая из этих структур является хиральной. Существование двух энантиомеров в данном случае обусловлено атомом углерода, имеющим четыре различных заместителя. Такой  Optical isomers (stereoisomers) are spatial isomers, the molecules of which are related to each other as an object and an incompatible mirror image (like the left and right hands). Two such stereoisomers are called enantiomers, and each of these structures is chiral. The existence of two enantiomers in this case is due to a carbon atom having four different substituents. Such
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) асимметрический атом углерода называют стереоцентром или хиральным центром. Смесь равных количеств обоих энантиомеров называется рацемической. SUBSTITUTE SHEET (RULE 26) an asymmetric carbon atom is called a stereocenter or chiral center. A mixture of equal amounts of both enantiomers is called racemic.
Подробное описание  Detailed description
Один из основных объектов, составляющих настоящее изобретение, был получен авторами в виде новых производных гидрированных пиpидo[4,3-b]индoлoв, замещенных в пиперидеиновом фрагменте по положениям 1 и/или 3, в виде оснований или их солей с фармакологически приемлимыми кислотами, а также в виде отдельных оптических изомеров или смесей последних, что в совокупности представлено общей формулой I,  One of the main objects constituting the present invention was obtained by the authors in the form of new derivatives of hydrogenated pyrido [4,3-b] indoles substituted in the piperidine moiety at positions 1 and / or 3, in the form of bases or their salts with pharmacologically acceptable acids, as well as in the form of individual optical isomers or mixtures of the latter, which together are represented by the general formula I,
Figure imgf000012_0001
Figure imgf000012_0001
в которой: wherein:
Z означает необязательно замещенные -(CH2)m-, -(CH2)mNH-, -(CH2)mO- или -(CH2)mS-; т может принимать значения 2, 3 и 4; Z is optionally substituted - (CH 2 ) m -, - (CH 2 ) m NH—, - (CH 2 ) m O— or - (CH 2 ) m S—; m can take values 2, 3 and 4;
знак (#) здесь и далее обозначает возможность наличия хирального центра; the sign (#) hereinafter indicates the possibility of a chiral center;
Ar представляет необязательно замещенные арил или гетарил, например, такие, как нафталин, пиридин, пиперидин, индол, бензимидазол, бензоксазол, бензотиазол, индазол, пиримидин, триазин, хинолин, изохинолин, хиназолин, хиноксалин и подобные;  Ar is optionally substituted aryl or hetaryl, for example, such as naphthalene, pyridine, piperidine, indole, benzimidazole, benzoxazole, benzothiazole, indazole, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
Rl представляет H, необязательно замещенный алкил, необязательно замещенный алкокси, галоген, ОН, СFЗ, CN, СFЗО, необязательно замещенную амино-группу, ацильную группу, необязательно замещенный арил или гетарил, алкенил, алкинил, аралкил, алкоксикарбонил, сульфонил, сульфинил, необязательно замещенный аминосульфонил и прочие; Rl также означает возможность наличия аннелированного цикла, например, сформированного такими фрагментами, как метилендиокси, этилендиокси и т.п.;  Rl is H, optionally substituted alkyl, optionally substituted alkoxy, halogen, OH, CF3, CN, CFZO, optionally substituted amino group, acyl group, optionally substituted aryl or hetaryl, alkenyl, alkynyl, aralkyl, alkoxycarbonyl, sulfonyl, sulfinyl, optionally substituted amino-sulfonyl and the like; Rl also means the possibility of the presence of an annelated cycle, for example, formed by fragments such as methylenedioxy, ethylenedioxy, etc .;
R2 представляет H, метил, необязательно замещенные алкил или бензил;  R2 represents H, methyl, optionally substituted alkyl or benzyl;
RЗ и R4 представляют H, метил, необязательно замещенный алкил, или мостик соединяющий положения цикла, состоящий из двух или трех атомов углерода; RЗ и R4 не могут одновременно представлять H: RЗ = R4 ф H.  R3 and R4 are H, methyl, optionally substituted alkyl, or a bridge connecting two or three carbon atoms; R3 and R4 cannot simultaneously represent H: R3 = R4 f H.
Среди соединений формулы I предпочтительными являются следующие подгруппы соединений, являющиеся производными 2,3,4,5-тeтpaгидpo-7H-пиpидo[4,3- όjиндола, замещенными по положениям 1 и/или 3, и представленные общими формулами 1-1, 1-2, 1-3, 1-4 и 1-5:  Among the compounds of formula I, the following subgroups of compounds are preferred which are derivatives of 2,3,4,5-tetrahydro-7H-pyrido [4,3-ό jindole, substituted at positions 1 and / or 3, and represented by general formulas 1-1, 1 -2, 1-3, 1-4 and 1-5:
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26)
Figure imgf000013_0001
SUBSTITUTE SHEET (RULE 26)
Figure imgf000013_0001
1.1 I.2 1.3
Figure imgf000013_0002
в которых: 1.1 I.2 1.3
Figure imgf000013_0002
in which:
Q означает необязательно замещенные группы -CH2CH2- или -CH2CH2O-; Q is optionally substituted —CH 2 CH 2 - or —CH 2 CH 2 O—;
Аlkl представляет метил или этил;  Alkl is methyl or ethyl;
ArI представляет необязательно замещенные фенил или 6-члeнный азагетероцикл, например, такие, как фенил, пиридин, пиперидин, пиримидин, триазин, хинолин, изохинолин, хиназолин, хиноксалин и подобные;  ArI is optionally substituted phenyl or a 6-membered azaheterocycle, for example, such as phenyl, pyridine, piperidine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
Rl и R2 имеют значения, определенные выше.  Rl and R2 are as defined above.
Среди соединений, представленных формулами 1-1, 1-2, 1-3, 1-4 и 1-5, предпочтительными являются стереоизомерно чистые (siпglе isоmеr) подгруппы веществ, представленных общими формулами Ll.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2:  Among the compounds represented by formulas 1-1, 1-2, 1-3, 1-4 and 1-5, stereoisomerically pure (siпгре isomer) subgroups of the substances represented by general formulas Ll.1, 1.1.2, 1.2.1 are preferred , 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2:
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26)
Figure imgf000014_0001
SUBSTITUTE SHEET (RULE 26)
Figure imgf000014_0001
1.1.1 1.1.2 1.2.1 I.2.2 1.1.1 1.1.2 1.2.1 I.2.2
Figure imgf000014_0002
Figure imgf000014_0002
1.3.1 1.3.2 I.З.З 1.3.4  1.3.1 1.3.2 I.З.З 1.3.4
Figure imgf000014_0003
Figure imgf000014_0003
в которых: in which:
ArI, Rl, R2 и Q имеют значения, определенные выше.  ArI, Rl, R2, and Q are as defined above.
Наиболее предпочтительными являются следующие отдельные соединения, представленные формулами 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2, которые могут быть в виде свободных оснований и/или в виде их фармакологически приемлемых солей:  Most preferred are the following individual compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1 , 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2, which may be in the form of free bases and / or in the form of their pharmacologically acceptable salts:
1. 1 ,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  1.1, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-N-pyrido [4,3-b] indole
2. l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  2. l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
3. l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  3. l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
4. l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  4. l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
5. l,3,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 5. l, 3,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
6. l,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 6. l, 3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
7. l,3,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 7. l, 3,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
8. l,3,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл8. l, 3,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
9. 8-мeтoкcи-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 9. 8-methoxy-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
10. 8-мeтoкcи-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  10. 8-methoxy-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 11. 8-мeтoкcи- 1 ,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpό- 1 H-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 11. 8-methoxy-1, 3-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydra-1 H-pyrido [4,3-b] indole
12. 8-мeтoкcи-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  12. 8-Methoxy-l, 3-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
13. 8-фтop-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 13. 8-fluoro-1, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
14. 8-фтop-l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл14. 8-fluor-l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
15. l,2,3,6-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 15. l, 2,3,6-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
16. 8-xлop-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 16. 8-chlorop-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
17. 8-xлop-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл17. 8-chlorop-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
18. 8-xлop-l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-χeтpaгидpo-lH-пиpидo[4,3-b]индoл18. 8-chlorop-l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-χ-tetrahydro-lH-pyrido [4,3-b] indole
19. 8-xлop-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Щ-пиpидo[4,3-b]индoл19. 8-chlorop-l, 3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-Щ-pyrido [4,3-b] indole
20. 8-бpoм-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл20. 8-bromo-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
21. 8-бpoм-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл21. 8-bromo-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
22. 8-бpoм- 1 ,3 -димeтил-5 -(2-пиpидин-З -илэтил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b] индол22. 8-bromo-1, 3-dimethyl-5 - (2-pyridin-3-ethylethyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
23. 8-бpoм-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл23. 8-bromo-l, 3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
24. 8-фтop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл24. 8-fluoro-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
25. 3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 25. 3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
26. 3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  26. 3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
27. 8-xлop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 27. 8-chlorop-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
28. 3,7,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл28. 3,7,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
29. 3,7,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 29. 3,7,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
30. 3,7,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 30. 3,7,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
31. 3,7,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл31. 3,7,9-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
32. 3,8-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл32. 3,8-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
33. 3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 33. 3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
34. 3,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 34. 3,8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
35. 3,8-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл35. 3,8-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
36. 6-фтop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл36. 6-fluoro-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
37. 3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaтидpo-Ш-пиpидo[4,3-b]индoл 37. 3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetratidro-III-pyrido [4,3-b] indole
38. 3,6-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 38. 3,6-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
39. 6-xлop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл39. 6-chlorop-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
40. 8-мeтoкcи-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Щ-пиpидo[4,3-b]индoл40. 8-Methoxy-3-methyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetrahydro-Sch-pyrido [4,3-b] indole
41. 8-мeтoкcи-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 41. 8-methoxy-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
42. 8-мeтoкcи-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 42. 8-methoxy-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
43. 8-мeтoкcи-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 43. 8-methoxy-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
13 13
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 44. 8-фтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2^3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoлSUBSTITUTE SHEET (RULE 26) 44. 8-fluoro-3-methyl-5- (2-pyridin-2-yl-ethyl) -2 ^ 3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
45. 8-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 45. 8-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
46. 8-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 46. 8-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
47. 8-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл47. 8-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
48. 2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 48. 2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
49. 2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  49. 2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
50. 2-бeнзил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  50. 2-benzyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
51. 2,3,7,9-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  51. 2,3,7,9-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
52. 2-этил-3,7,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 52. 2-ethyl-3,7,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
53. 8-бpoм-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3-b]индoл 53. 8-bromo-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
54. 2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  54. 2,3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
55. 2-этил-3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  55. 2-ethyl-3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
56. 2-бeнзил-3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  56. 2-benzyl-3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
57. 8-этил-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  57. 8-ethyl-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
58. 2,8-диэтил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  58. 2,8-diethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
59. 6-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 59. 6-fluorop-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
60. 2,3,6,9-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 60. 2,3,6,9-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
61. 2-этил-3,6,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 61. 2-ethyl-3,6,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
62. 6-xлop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл62. 6-chlorop-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
63. 8-изoпpoпил-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeτpaгидpo-Ш-пиpидo[4,3-b]индoл63. 8-isopropyl-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
64. 6,8-дифтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл64. 6,8-difert-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
65. 6,8-дифтop-3-мeтил-5-(2-фeнилэтил)-2,3,4т5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 65. 6,8-difert-3-methyl-5- (2-phenylethyl) -2,3,4t5-tetrahydro-lH-pyrido [4,3-b] indole
66. l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  66. l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
67. 2,3,6-τpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-l.H-пиpидo[4,3-b]индoл  67. 2,3,6-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-l.H-pyrido [4,3-b] indole
68. 2-этил-3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  68. 2-ethyl-3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
69. 2-бeнзил-3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 69. 2-benzyl-3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
70. 8-мeтoкcи-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл70. 8-Methoxy-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
71. 2-этил-8-мeтoкcи-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл71. 2-ethyl-8-methoxy-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
72. l,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 72. l, 8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
73. 8-этoкcи-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  73. 8-ethoxy-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
74. l,6-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  74. l, 6-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
75. l,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  75. l, 6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
76. 8-фтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  76. 8-fluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
77. 2-этил-8-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 77. 2-ethyl-8-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
78. 8-мeтoкcи-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 78. 8-methoxy-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
14 fourteen
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 79. 8-xлop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoлSUBSTITUTE SHEET (RULE 26) 79. 8-chlorop-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
80. 8-xлop-2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл80. 8-chlorop-2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
81. 8-мeтoкcи-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл81. 8-methoxy-l-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
82. 8-бpoм-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл82. 8-bromo-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
83. 8-фтop-l-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 83. 8-fluorop-l-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
84. 8-фтop-l-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 84. 8-fluor-l-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
85. 8-фтop-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл85. 8-fluorop-l-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
86. 8-xлop-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 87. 8 -хлор- 1 -метил- 5 -(2-фeнилэтил)-2 ,3 ,4 ,5 -тетраги дро- 1 Н-пири до [4 , 3 -b] индол 86. 8-chlorop-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole 87.8-chloro-1 -methyl- 5 - (2-phenylethyl) -2, 3, 4, 5-tetrages dro-1 N-pyri to [4, 3-b] indole
88. 6-фтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 88. 6-fluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
89. 2-этил-6-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл89. 2-ethyl-6-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
90. 8-бpoм-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл90. 8-bromo-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
91. 6-xлop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл91. 6-chlorop-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
92. 6-xлop-2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл92. 6-chlorop-2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
93. 8-бpoм-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл93. 8-bromo-l-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
94. 6,8-дифтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл94. 6,8-difluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
95. 2-этил-6,8-дифтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл95. 2-ethyl-6,8-difop-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
96. l-мeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл 96. l-methyl-8- (methylcylphonyl) -5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
97. 6-фтop-2,3,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 97. 6-fluoro-2,3,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
98. 2-этил-6-фтop-3,9-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл98. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
99. l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 99. l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
100. l,2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 100. l, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
101. l,2,6-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл101. l, 2,6-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
102. 8-мeтoкcи-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол 102. 8-methoxy-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
103. 8-фтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 103. 8-fluoro-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
104. 8-xлop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл104. 8-chlorop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
105. 6-фтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-диpидo[4,3-b]индoл105. 6-fluorop-1, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-dirido [4,3-b] indole
106. 6-xлop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл106. 6-chlorop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
107. 6,8-дифтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 107. 6,8-diptop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
108. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  108. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-phenylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
15 fifteen
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 109. 12-мeтил-5-(2-фeнилэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l U SUBSTITUTE SHEET (RULE 26) 109. 12-methyl-5- (2-phenylethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l U
эпиминoциклooктa[b]индoл epiminocycloocta [b] indole
110. 2,12-димeтил-5-(2-фeнилэтил)-6,7,8,9, 10,11 -гeкcaгидpo-5H-7, 11 - эпиминoциклooктa[b]индoл  110. 2,12-dimethyl-5- (2-phenylethyl) -6,7,8,9, 10,11-hexahydro-5H-7, 11 - epiminocyclooct [b] indole
111. 1 l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  111. 1 l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
112. 2,11 -димeтил-5-(2-фeнилэтил)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  112. 2,11-dimethyl-5- (2-phenylethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
113. 2-мeтoкcи-l l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  113. 2-methoxy-l l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
114. 2-фтop-l l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоцикл oгeптa[b] индол  114. 2-ftop-l l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocycle of the [b] indole
115. 2-xлop-l l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоцикл oгeптa[b] индол  115. 2-chlorop-l l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocycle of the drug [b] indole
116. l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b] индол  116. l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
117. l,2,3,8-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  117. l, 2,3,8-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
118. 1 ,2,3,6-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  118. 1, 2,3,6-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
119. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  119. 8-methoxy-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
120. 8-фтop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш- пиpидo[4,3-b]индoл  120. 8-fluor-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
121. 8-xлop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  121. 8-chlorop-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
122. 6-фтop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  122. 6-fluoro-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
123. 6-xлop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  123. 6-chlorop-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
124. 2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 124. 2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
125. 2-этил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 125. 2-ethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
126. 2,3,7,9-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  126. 2,3,7,9-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
16 16
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 127. 2-этил-3,7,9-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 127. 2-ethyl-3,7,9-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
128. 2,3,8-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  128. 2,3,8-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
129. 2-этил-3,8-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  129. 2-ethyl-3,8-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
130. 8-этил-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  130. 8-ethyl-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
131. 2,8-диэтил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  131. 2,8-diethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
132. 2,3,6,9-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  132. 2,3,6,9-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
133. 2-этил-3 ,6,9-тpимeтил-5 - [2-(4-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -bjиндол  133. 2-ethyl-3, 6,9-trimethyl-5 - [2- (4-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-bjindole
134. 2,3,6-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  134. 2,3,6-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
135. 2-этил-3,6-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  135. 2-ethyl-3,6-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
136. 8-мeтoкcи-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-τeтpaгидpo-Ш- пиридо [4,3 -b]индoл  136. 8-methoxy-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
137. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  137. 2-ethyl-8-methoxy-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
138. 8-этoкcи-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  138. 8-ethoxy-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
139. 8-фтop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  139. 8-fluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
140. 2-этил-8-фтop-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  140. 2-ethyl-8-fluoro-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
141. 8-xлop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  141. 8-chlorop-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
142. 8-xлop-2-этил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  142. 8-chlorop-2-ethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
143. 6-фтop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  143. 6-fluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
17 17
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 144. 2-этил-6-фтop-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 144. 2-ethyl-6-fluoro-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
145. 6-xлop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b] индол  145. 6-chlorop-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
146. 6-xлop-2-этил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш- пиридо [4,3-b] индол  146. 6-chlorop-2-ethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetra-para-Sh-pyrido [4,3-b] indole
147. 6,8-дифтop-2,3-димeтил-5-[2-(4-мeтилфeнил)эχил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  147. 6,8-difluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ehyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
148. 2-этил-6,8-дифтop-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  148. 2-ethyl-6,8-difop-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
149. 6-фтop-2,3,9-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  149. 6-fluoro-2,3,9-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
150. 2-этил-6-фтop-3,9-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  150. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
151. 1 ,2-димeтил-5 - [2-(4-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b]индoл 151. 1, 2-dimethyl-5 - [2- (4-methylphenyl) ethyl] -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
152. l,2,8-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 152. l, 2,8-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
153. 8-этил-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  153. 8-ethyl-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
154. l,2,6-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  154. l, 2,6-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
155. 8-мeтoкcи-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3-b] индол  155. 8-methoxy-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
156. 8-этoкcи-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  156. 8-ethoxy-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
157. 8-фтop-l,2-димeтил-5-[2-(4-мeтилфeйил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  157. 8-fluorop-l, 2-dimethyl-5- [2- (4-methylphyyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
158. 8-xлop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  158. 8-chlorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
159. 6-фтop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  159. 6-fluorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
160. 6-xлop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  160. 6-chlorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
161. 6,8-дифтop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  161. 6,8-diptop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
П ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 162. l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -b] индол SUBSTITUTE SHEET (RULE 26) 162. l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
163. 12-мeтил-5-[2-(4-мeтилфeнил)этил]-6,7, 8,9,10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  163. 12-methyl-5- [2- (4-methylphenyl) ethyl] -6,7, 8,9,10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
164. 2,12-димeтил-5-[2-(4-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  164. 2,12-dimethyl-5- [2- (4-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
165. l l-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  165. l l-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
166. 2,1 l-димeтил-5-[2-(4-мeтилфeнил)этил]-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  166. 2,1 l-dimethyl-5- [2- (4-methylphenyl) ethyl] -5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
167. 2-мeтoкcи- 11 -мeтил-5-[2-(4-мeтилфeнил)этил]-'5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол 167. 2-methoxy-11-methyl-5- [2- (4-methylphenyl) ethyl] - ' 5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
168. 2-фтop-l l-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  168. 2-fluorop-l-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
169. 2-xлop- 11 -мeтил-5-[2-(4-мeтилфeнил)этил]-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  169. 2-chloro-11-methyl-5- [2- (4-methylphenyl) ethyl] -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
170. l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  170. l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
171. l,2,3,8-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  171. l, 2,3,8-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
172. l,2,3,6-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  172. l, 2,3,6-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
173. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  173. 8-methoxy-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
174. 8-фтop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] индол  174. 8-fluoro-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
175. 8-xлop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индол  175. 8-chlorop-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
176. 6-фтop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш- пиридо [4 , 3 -b] индол  176. 6-fluoro-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetra-para-Sh-pyrido [4, 3-b] indole
177. 6-xлop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  177. 6-chlorop-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
178. 2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 178. 2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
179. 2,3,7,9-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 179. 2,3,7,9-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
19 19
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 180. 2-этил-3,7,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 180. 2-ethyl-3,7,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
181. 2,3,8-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  181. 2,3,8-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
182. 2-этил-3,8-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  182. 2-ethyl-3,8-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
183. 8-этил-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  183. 8-ethyl-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
184. 2,8-диэтил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  184. 2,8-diethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
185. 2,ЗД9-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  185. 2, ZD9-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
186. 2-этил-3,6,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  186. 2-ethyl-3,6,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
187. 2,3,6-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  187. 2,3,6-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
188. 2-этил-3,6-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  188. 2-ethyl-3,6-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
189. 8-мeтoкcи-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  189. 8-methoxy-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
190. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  190. 2-ethyl-8-methoxy-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
191. 8-этoкcи-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] индол  191. 8-ethoxy-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
192. 8-фтop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  192. 8-fluoro-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
193. 2-этил-8-фтop-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  193. 2-ethyl-8-fluoro-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
194. 8-xлop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  194. 8-chlorop-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
195. 8-xлop-2-этил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  195. 8-chlorop-2-ethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
196. 6-фтop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  196. 6-fluoro-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
20 twenty
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 197. 2-этил-6-фтop-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 197. 2-ethyl-6-fluoro-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
198. 6-xлop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  198. 6-chlorop-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
199. 6-xлop-2-этил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  199. 6-chlorop-2-ethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
200. 6,8-дифтop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  200. 6,8-difluoro-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
201. 2-этил-6,8-дифтop-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  201. 2-ethyl-6,8-difop-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
202. 6-фтop-2,3,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  202. 6-fluoro-2,3,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
203. 2-этил-6-фтop-3,9-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] индол  203. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
204. l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 204. l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
205. l,2,8-тpимeтил-5-[2-(2-мeτилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 205. l, 2,8-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
206. 8-этил-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  206. 8-ethyl-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
207. l,2,6-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  207. l, 2,6-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
208. 8-мeтoкcи-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  208. 8-methoxy-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
209. 8-фтop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  209. 8-fluorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
210. 8-xлop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  210. 8-chlorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
211. 6-фтop-l ,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  211. 6-fluorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
212. 6-xлop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  212. 6-chlorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
213. 6,8-дифтop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  213. 6,8-diptop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
214. l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- 1 Н-пири до [4 , 3 -b] индол  214. l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-1 H-pyri to [4, 3-b] indole
21 21
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 215. 12-мeтил-5-[2-(2-мeтилфeнил)этил]-6, 7,8,9,10, 1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл SUBSTITUTE SHEET (RULE 26) 215. 12-methyl-5- [2- (2-methylphenyl) ethyl] -6, 7,8,9,10, 1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
216. 2,12-димeтил-5-[2-(2-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  216. 2,12-dimethyl-5- [2- (2-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
217. 11 -мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  217. 11-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
218. 2,11 -димeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминоцикл oгeптa[b] индол  218. 2,11-dimethyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocycle of the [b] indole
219. 2-мeтoкcи- 11 -мeтил-5-[2-(2-мeтилфeнил)этил] -5,6,7,8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  219. 2-methoxy-11-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
220. 2-фтop-l l-мeтил-5-[2-(2-мeтилфeнил)этил]-5,6s7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл 220. 2-fluorop-l l-methyl-5- [2- (2-methylphenyl) ethyl] -5.6 s 7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
221. 2-xлop- 11 -мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминоцикл oгeптa[b] индол  221. 2-chloro-11-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocycle of the [b] indole
222. l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  222. l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
223. l,2,3,8-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  223. l, 2,3,8-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
224. 1,2,3, 6-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  224. 1,2,3, 6-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
225. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  225. 8-methoxy-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
226. 8-фтop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  226. 8-fluor-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-bjindole
227. 8-xлop- 1 ,2,3 -тpимeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4 , 3 -b] индол  227. 8-chloro-1, 2,3-trimethyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4, 3-b] indole
228. 6-фтop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  228. 6-fluor-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
229. 6-xлop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] ин дол  229. 6-chlorop-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] in dol
230. 2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 230. 2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
231. 2-этил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 231. 2-ethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
232. 2,3,7,9-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  232. 2,3,7,9-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
22 22
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 233. 2-этил-3,7,9-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 233. 2-ethyl-3,7,9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
234. 2,3,8-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индoл  234. 2,3,8-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
235. 2-этил-3,8-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  235. 2-ethyl-3,8-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
236. 8-этил-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  236. 8-ethyl-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
237. 2,8-диэтил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  237. 2,8-diethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
238. 2,3,6,9-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  238. 2,3,6,9-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
239. 2-этил-3,6,9-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  239. 2-ethyl-3,6,9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
240. 2,3,6-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4j5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  240. 2,3,6-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4j5-tetrahydro-lH-pyrido [4,3-b] indole
241. 2-этил-3,6-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  241. 2-ethyl-3,6-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
242. 8-мeтoкcи-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  242. 8-methoxy-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
243. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] ин до л  243. 2-ethyl-8-methoxy-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] in to l
244. 8 -этoкcи-2 , 3 - димети л- 5 - [2-(3 -мети лфени л)этил] -2,3,4,5 -тетраги дро- 1 H- пиpидo[4,3-b]индoл  244. 8-ethoxy-2, 3 - dimethyl l-5 - [2- (3-methyl lphenyl l) ethyl] -2,3,4,5-tetrages dro-1 H-pyrido [4,3-b] indole
245. 8-фтop-2,3-димeтил-5-[2-(3-мeтилфeнил)эfил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  245. 8-fluoro-2,3-dimethyl-5- [2- (3-methyl-phenyl) -ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
246. 2-этил-8-фтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  246. 2-ethyl-8-fluoro-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
247. 8-xлop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  247. 8-chlorop-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
248. 8-xлop-2-этил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  248. 8-chlorop-2-ethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
249. 6-фтop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  249. 6-fluoro-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
23 23
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 250. 2-этил-6-фтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол SUBSTITUTE SHEET (RULE 26) 250. 2-ethyl-6-fluoro-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
251. 6-xлop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  251. 6-chlorop-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
252. 6-xлop-2-этил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  252. 6-chlorop-2-ethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
253. 6,8-дифтop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  253. 6,8-difluoro-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
254. 2-этил-6,8-дифтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  254. 2-ethyl-6,8-difop-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
255. 6-фтop-2,3,9-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  255. 6-fluoro-2,3,9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
256. 2-этил-6-фтop-3,9-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  256. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
257. l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 257. l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
258. l,2,8-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 258. l, 2,8-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
259. 8-этил-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  259. 8-ethyl-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
260. l,2,6-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  260. l, 2,6-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
261. 8-мeтoкcи- 1 ,2-димeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -b]индoл  261. 8-methoxy-1, 2-dimethyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
262. 8-этoкcи-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  262. 8-ethoxy-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
263. 8-фтop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  263. 8-fluorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
264. 8-xлop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  264. 8-chlorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
265. 6-фτop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  265. 6-fluoro-1, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
266. 6-xлop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  266. 6-chlorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
267. 6,8-дифтop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  267. 6,8-diptop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
24 24
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 268. 1 ,2-димeтил-5 - [2-(3 -мeтилфeнил)этил] -8-(мeтилcyльфoнил)-2,3 ,4,5 -тетраги дро- 1 Н-пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 268. 1, 2-dimethyl-5 - [2- (3-methylphenyl) ethyl] -8- (methylcylphonyl) -2.3, 4,5-tetrages dro-1 N-pyrido [4,3 -b] indole
269. 12-мeтил-5-[2-(3-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  269. 12-methyl-5- [2- (3-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
270. 2,12-димeтил-5-[2-(3-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  270. 2,12-dimethyl-5- [2- (3-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
271. l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  271. l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
272. 2, 11 -димeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  272. 2, 11-dimethyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
273. 2-мeтoкcи-l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoreптa[b] индол  273. 2-methoxy-l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclorepta [b] indole
274. 2-фтop-l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  274. 2-fluorop-l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
275. 2-xлop-l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  275. 2-chlorop-l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
276. 5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  276. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
277. 5-[2-(4-фтopфeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  277. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
278. 5-[2-(4-фтopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  278. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
279. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  279. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
280. 8-фтop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  280. 8-fluorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
281. 8-xлop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  281. 8-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
282. 6-фтop-5-[2-(4-фтopфeнил)эτил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индол  282. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
283. 6-xлop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  283. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
284. 5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 284. 5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
285. 2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 285. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
25 25
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 286. 5-[2-(4-фтopфeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 286. 5- [2- (4-fluorophenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
287. 2-этил-5-[2-(4-фтopфeнил)этил]-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  287. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,7,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
288. 5-[2-(4-фтopфeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  288. 5- [2- (4-fluorophenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
289. 2-этил-5-[2-(4-фтopфeнил)этил]-3,8-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  289. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,8-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
290. 8-этил-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  290. 8-ethyl-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
291. 2,8-диэтил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  291. 2,8-diethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
292. 5-[2-(4-фтopфeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  292. 5- [2- (4-fluorophenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
293. 2-этил-5-[2-(4-фтopфeнил)этил]-3,6,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  293. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,6,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
294. 5-[2-(4-фтopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-ДH-пиpидo[4,3- b] индол  294. 5- [2- (4-fluorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-DH-pyrido [4,3-b] indole
295. 2-этил-5-[2-(4-фтopфeнил)этил]-3,6-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  295. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,6-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
296. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  296. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
297. 2-этил-5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  297. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -8-methoxy-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
298. 8-этoкcи-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  298. 8-ethoxy-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
299. 8-фтop-5 - [2-(4-фтopфeнил)этил] -2,3 -димeтил-2,3 ,4,5 -тетрагидро- 1 H-пиpидo[4,3 - b] индол  299. 8-fluorop-5 - [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
300. 2-этил-8-фтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  300. 2-ethyl-8-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
301. 8-xлop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  301. 8-chlorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
302. 8-xлop-2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  302. 8-chlorop-2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
26 26
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 303. 6-фтop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 303. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
304. 2-этил-6-фтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  304. 2-ethyl-6-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
305. 6-xлop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  305. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
306. 6-xлop-2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  306. 6-chlorop-2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
307. 6,8-дифтop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  307. 6,8-diptop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
308. 2-этил-6,8-дифтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  308. 2-ethyl-6,8-difop-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
309. 6-фтop-5-[2-(4-фтopфeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] индол  309. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
310. 2-этил-6-фтop-5-[2-(4-фтopфeнил)этил]-3,9-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  310. 2-ethyl-6-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -3,9-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
311. 5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 311. 5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
312. 5-[2-(4-фтopфeнил)этил]-l ,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 312. 5- [2- (4-fluorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
313. 8-этил-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,'3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 313. 8-Ethyl-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2 ', 3,4,5-tetrahydro-SH-pyrido [4,3- b] indole
314. 5-[2-(4-фтopфeнил)этил]-l,2,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  314. 5- [2- (4-fluorophenyl) ethyl] -l, 2,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
315. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  315. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
316. 8-этoкcи-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  316. 8-ethoxy-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
317. 8-фтop-5-[2-(4-фтopфeнил)этил]-l,2-яимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  317. 8-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -l, 2-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
318. 8-xлop-5 - [2-(4-фтopфeнил)этил] - 1 ,2-димeтил-2,3 ,4,5-тeтpaгидpo- 1 H-пиpидo[4,3 - b] индол  318. 8-chlorop-5 - [2- (4-fluorophenyl) ethyl] - 1, 2-dimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
319. 6-фтop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  319. 6-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
320. 6-xлop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  320. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
27 27
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 321. 6,8-дифтop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 321. 6,8-diptop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
322. 5-[2-(4-фтopфeнил)этил]-l,2-димeтил-8-(мeтил'cyльфoнил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл 322. 5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-8- (methyl ' sulfonyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
323. 5-[2-(4-фтopфeнил)этил]-12-мeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  323. 5- [2- (4-fluorophenyl) ethyl] -12-methyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
324. 5-[2-(4-фтopфeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7Д 1- эпиминoциклooктa[b]индoл  324. 5- [2- (4-fluorophenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7D 1-epiminocyclooct [b] indole
325. 5-[2-(4-фтopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  325. 5- [2- (4-fluorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
326. 5-[2-(4-фтopфeнил)этил]-2,l l-димeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  326. 5- [2- (4-fluorophenyl) ethyl] -2, l l-dimethyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
327. 5-[2-(4-фтopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  327. 5- [2- (4-fluorophenyl) ethyl] -2-methoxy-l l-methyl-5,6,7,8,9,10-reccahydro-7,10-epiminocyclohepta [b] indole
328. 2-фтop-5-[2-(4-фтopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  328. 2-fluorop-5- [2- (4-fluorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
329. 2-xлop-5-[2-(4-фтopфeнил)этил]- 11 -мeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  329. 2-chlorop-5- [2- (4-fluorophenyl) ethyl] - 11-methyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
330. 5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  330. 5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
331. 5-[2-(4-xлopфeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  331. 5- [2- (4-chlorophenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
332. 5-[2-(4-xлopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  332. 5- [2- (4-chlorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
333. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  333. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
334. 5-[2-(4-xлopфeнил)этил]-8-фтop-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  334. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
335. 8-xлop-5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индол  335. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
336. 5-[2-(4-xлopфeнил)этил]-6-фтop-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] ин дол  336. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4, 3-b] in dol
337. 6-xлop-5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  337. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
338. 5-[2-(4-xлopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lЦ;Пиpидo[4,3-b]индoл  338. 5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lC; Pyrido [4,3-b] indole
28 28
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 339. 5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 339. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
340. 5-[2-(4-xлopфeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  340. 5- [2- (4-chlorophenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
341. 5-[2-(4-xлopфeнил)этил]-2-этил-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  341. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,7,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
342. 5-[2-(4-xлopфeнил)этил]-2,3,8-τpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  342. 5- [2- (4-chlorophenyl) ethyl] -2,3,8-τ-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
343. 5-[2-(4-xлopфeнил)этил]-2-этил-3,8-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  343. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,8-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
344. 5-[2-(4-xлopфeнил)этил]-8-этил-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  344. 5- [2- (4-chlorophenyl) ethyl] -8-ethyl-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
345. 5-[2-(4-xлopфeнил)этил]-2,8-диэтил-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  345. 5- [2- (4-chlorophenyl) ethyl] -2,8-diethyl-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
346. 5-[2-(4-xлopфeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  346. 5- [2- (4-chlorophenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
347. 5-[2-(4-xлopфeнил)этил]-2-этил-3,6,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  347. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,6,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
348. 5-[2-(4-xлopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  348. 5- [2- (4-chlorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
349. 5-[2-(4-xлopфeнил)этил]-2-этил-3,6-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- bjиндол  349. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,6-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
350. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  350. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
351. 5-[2-(4-xлopфeнил)этил]-2-этил-8-мeтoкcи-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индол  351. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-8-methoxy-3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
352. 5-[2-(4-xлopфeнил)этил]-8-фтop-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  352. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
353. 5 - [2-(4-xлopфeнил)этил] -2-этил-8-фтop-3 -мeтил-2,3 ,4,5 -тетр'агидро- 1 H- пиридо [4,3 -b] индол 353. 5 - [2- (4-chlorophenyl) ethyl] -2-ethyl-8-ftop-3-methyl-2,3, 4,5-tetra ' agidro-1 H-pyrido [4,3 -b] indole
354. 8-xлop-5-[2-(4-xлopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  354. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
355. 8-xлop-5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  355. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
29 29th
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 356. 5- [2-(4-xлopфeнил)этил] -6-фтop-2,3 -димeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол SUBSTITUTE SHEET (RULE 26) 356. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-2,3-dimethyl-2,3,4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
357. 5-[2-(4-xлopфeнил)этил]-2-этил-6-фтop-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  357. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-6-fluoro-3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
358. 6-xлop-5-[2-(4-xлopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  358. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
359. 6-xлop-5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  359. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
360. 5-[2-(4-xлopфeнил)этил]-6,8-дифтop-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  360. 5- [2- (4-chlorophenyl) ethyl] -6,8-difluoro-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
361. 5-[2-(4-xлopфeнил)этил]-2-этил-6,8-дифтop-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-bjиндол  361. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-6,8-diftop-3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
362. 5-[2-(4-xлopфeнил)этил]-6-фтop-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  362. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-2,3,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
363. 5-[2-(4-xлopфeнил)этил]-2-этил-6-фтop-3,9-димeтил-2,3,4,5-тетрагидро-1H- пиридо[4,3-b]индол  363. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-6-fluoro-3,9-dimethyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole
364. 5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 364. 5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
365. 5-[2-(4-xлopфeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 365. 5- [2- (4-chlorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
366. 5-[2-(4-xлopфeнил)этил]-8-этил-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  366. 5- [2- (4-chlorophenyl) ethyl] -8-ethyl-l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
367. 5-[2-(4-xлopфeнил)этил]-l,2,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  367. 5- [2- (4-chlorophenyl) ethyl] -l, 2,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
368. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  368. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-Ш-pyrido [4,3-b] indole
369. 5-[2-(4-xлopфeнил)этил]-8-фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  369. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
370. 8-xлop-5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  370. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
371. 5-[2-(4-xлopфeнил)этил]-6-фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  371. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
372. 6-xлop-5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  372. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
373. 5-[2-(4-xлopфeнил)этил]-6,8-дифтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индол  373. 5- [2- (4-chlorophenyl) ethyl] -6,8-diflt-l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
30 thirty
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 374. 5-[2-(4-xлopфeнил)этил]-12-мeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл SUBSTITUTE SHEET (RULE 26) 374. 5- [2- (4-chlorophenyl) ethyl] -12-methyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
375. 5-[2-(4-xлopфeнил)этил]-2, 12-димeтил-6,7, 8,9,10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  375. 5- [2- (4-chlorophenyl) ethyl] -2, 12-dimethyl-6,7, 8,9,10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
376. 5-[2-(4-xлopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  376. 5- [2- (4-chlorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [b] indole
377. 5-[2-(4-xлopфeни'л)этил]-2,l l-димeтил-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b] индол 377. 5- [2- (4-chloropheni ' l) ethyl] -2, l l-dimethyl-5,6,7,8,9,10-recahydro-7,10-epiminocyclohepta [b] indole
378. 5-[2-(4-xлopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  378. 5- [2- (4-chlorophenyl) ethyl] -2-methoxy-l l-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
379. 5-[2-(4-xлopфeнил)этил]-2-фтop-l l-мeтил-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  379. 5- [2- (4-chlorophenyl) ethyl] -2-fluor-l-methyl-5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
380. 2-xлop-5-[2-(4-xлopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcarидpo-7,10- эпиминoциклoгeптa[b] индол  380. 2-chlorop-5- [2- (4-chlorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexcaridro-7,10-epiminocyclogen [b] indole
381. 5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  381. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
382. 5-[2-(4-мeтoкcифeнил)этил]-1,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-IH- пиридо[4,3-b]индoл  382. 5- [2- (4-methoxyphenyl) ethyl] -1,2,3,8-tetramethyl-2,3,4,5-tetrahydro-IH-pyrido [4,3-b] indole
383. 5-[2-(4-мeтoкcифeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  383. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
384. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  384. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
385. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  385. 8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
386. 8-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  386. 8-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
387. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимέтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  387. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-thrimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
388. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  388. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
389. 5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  389. 5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
390. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  390. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
31 31
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 391. 5-[2-(4-мeтoкcифeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтparидpo-Ш- пиридо[4,3-b]индол SUBSTITUTE SHEET (RULE 26) 391. 5- [2- (4-methoxyphenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
392. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  392. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,7,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
393. 5-[2-(4-мeтoкcифeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  393. 5- [2- (4-methoxyphenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
394. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,8-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  394. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,8-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
395. 8-этил-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индо л  395. 8-ethyl-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indo l
396. 2,8-диэтил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтp'aгидpo-lH- пиридо [4 , 3 -b] индол  396. 2,8-diethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
397. 5-[2-(4-мeтoкcифeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  397. 5- [2- (4-methoxyphenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
398. 2-этил-5 - [2-(4-мeтoкcифeнил)этил] -3 ,6,9-тpимeтил-2,3 ,4,5 -тетрагидро- 1 H- пиридо [4 ,3 -b] индол  398. 2-ethyl-5 - [2- (4-methoxyphenyl) ethyl] -3, 6,9-trimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4, 3-b] indole
399. 5-[2-(4-мeтoкcифeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  399. 5- [2- (4-methoxyphenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
400. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,6-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] ин до л  400. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,6-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] in to l
401. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  401. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
402. 2-этил-8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  402. 2-ethyl-8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Ш-pyrido [4, 3-b] indole
403. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  403. 8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
404. 2-этил-8-фтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  404. 2-ethyl-8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4, 3-b] indole
405. 8-xлop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтparидpo-lH- пиридо [4,3 -b] индол  405. 8-chlorop-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetraparidro-lH-pyrido [4,3 -b] indole
406. 8-xлop-2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  406. 8-chlorop-2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
407. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  407. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Ш-pyrido [4,3 -b] indole
32 32
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 408. 2-этил-6-фтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 408. 2-ethyl-6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
409. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтparидpo-Ш- пиридо [4,3 -bjиндол  409. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetraparidro-Sh-pyrido [4,3-bjindole
410. 6-xлop-2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  410. 6-chlorop-2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
411. 6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b]ин до л  411. 6,8-difert-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] in to l
412. 2-этил-6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  412. 2-ethyl-6,8-difop-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
413. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  413. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
414. 2-этил-6-фтop-5-[2-(4-мeтoкcифeнил)этил]-3,9-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] ин до л  414. 2-ethyl-6-fluorop-5- [2- (4-methoxyphenyl) ethyl] -3,9-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4, 3-b] in to l
415. 5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo:lH-пиpидo[4,3- b] индол 415. 5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro : lH-pyrido [4,3-b] indole
416. 5-[2-(4-мeтoкcифeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  416. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
417. 8-этил-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  417. 8-ethyl-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
418. 5-[2-(4-мeтoкcифeнил)этил]-l,2,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  418. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
419. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  419. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
420. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  420. 8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
421. 8-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтparидpo-lH- пиридо[4,3-b]индoл  421. 8-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
422. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  422. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
423. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,354,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол 423. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3 5 4,5-tetrahydro-Sh-pyrido [4,3-b] indole
424. 6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  424. 6,8-difert-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
33 33
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 425. 5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 425. 5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-8- (methylcylphonyl) -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
426. 5-[2-(4-мeтoкcифeнил)этил]-12-мeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  426. 5- [2- (4-methoxyphenyl) ethyl] -12-methyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
427. 5-[2-(4-мeтoкcифeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  427. 5- [2- (4-methoxyphenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocycloocta [b] indole
428. 5 - [2-(4-мeтoкcифeнил)этил] - 11 -мeтил-5 ,6 ,7,8,9^10-reкcaги дpo-7 ,10- эпиминoциклoгeптa[b] индол  428. 5 - [2- (4-methoxyphenyl) ethyl] - 11-methyl-5, 6, 7,8,9 ^ 10-reagents dpo-7, 10-epiminocyclohepta [b] indole
429. 5-[2-(4-мeтoкcифeнил)этил]-2, 11 -димeтил-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  429. 5- [2- (4-methoxyphenyl) ethyl] -2, 11-dimethyl-5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
430. 2-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  430. 2-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
431. 2-фтop-5-[2-(4-мeтoкcифeнил)этил]-l l-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  431. 2-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l l-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
432. 2-xлop-5-[2-(4-мeтoкcифeнил)этил]-l l-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  432. 2-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l l-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
433. l,2,3-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] индол  433. l, 2,3-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
434. l,2,3,8-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  434. l, 2,3,8-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
435. l,2,3,6-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пири до [4 ,3 -b] индол  435. l, 2,3,6-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Shpiri to [4, 3-b] indole
436. 8-фтop-l,2,3-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  436. 8-fluor-l, 2,3-thimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
437. 6-фтop-l,2,3-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтparидpo- Ш-пиpидo[4,3-b]индoл  437. 6-fluorop-l, 2,3-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
438. 2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  438. 2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
439. 2-этил-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  439. 2-ethyl-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
440. 2,3,7,9-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  440. 2,3,7,9-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
441. 2-этил-3,7,9-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  441. 2-ethyl-3,7,9-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
34 34
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 442. 2,3,8-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 442. 2,3,8-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
443. 2-этил-3,8-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  443. 2-ethyl-3,8-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
444. 8-этил-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил} -2,3,4, 5-тeтpaгидpo- IH- пиридо [4 , 3 -b] индол  444. 8-ethyl-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4, 5-tetrahydro-IH-pyrido [4, 3-b] indole
445. 2,3 ,6,9-тeтpaмeтил-5- {2- [4-(тpифтopмeтил)фeнил] этил } -2,3 ,4,5 -тетрагидро- 1 H- пиpидo[4,3-b]индoл  445. 2,3, 6,9-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
446. 2-этил-3,6,9-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  446. 2-ethyl-3,6,9-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
447. 2,3,6-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  447. 2,3,6-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
448. 2-этил-3,6-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  448. 2-ethyl-3,6-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
449. 8-мeтoкcи-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- lH-пиpидo[4,3-b]индoл  449. 8-methoxy-2,3-dimethyl-5- {2- [4- (trifomethyl) phenyl] ethyl} -2,3,4,5-tetrahydrol-lH-pyrido [4,3-b] indole
450. 8-фтop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил} -2,3,4, 5-тeтpaгидpo- IH- пиpидo[4,3-b]индoл  450. 8-fluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4, 5-tetrahydro-IH-pyrido [4,3-b] indole
451. 2-этил-8-фтop-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  451. 2-ethyl-8-fluoro-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
452. 8-xлop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  452. 8-chloro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
453. 6-фтop-2,3 -димeтил-5- { 2- [4-(тpифтopмeтил)фeнил] этил } -2,3 ,4,5 -тетрагидро- 1 H- пиpидo[4,3-b]индoл  453. 6-fluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
454. 2-этил-6-фтop-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -b]индoл  454. 2-ethyl-6-fluoro-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3 -b ] indole
455. 6-xлop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4 ,3 -b] индол  455. 6-chlorop-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
456. 6,8-дифтop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  456. 6,8-difluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
457. 6-фтop-2,3,9-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  457. 6-fluoro-2,3,9-trimethyl-5- {2- [4- (tri-methyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
458. 1 ,2-димeтил-5 - { 2-[4-(тpифтopмeтил)фeнил] этил } -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -b]индoл  458. 1, 2-dimethyl-5 - {2- [4- (triflumethyl) phenyl] ethyl} -2.3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
35 35
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) _ SUBSTITUTE SHEET (RULE 26) _
459. l,2,8-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  459. l, 2,8-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
460. 8-этил-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  460. 8-ethyl-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
461. l,2,6-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  461. l, 2,6-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
462. 8-мeтoкcи-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- lH-пиpидo[4,3-b]индoл  462. 8-methoxy-l, 2-dimethyl-5- {2- [4- (trifomethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
463. 8-фтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  463. 8-fluor-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
464. 8-xлop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  464. 8-chlorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
465. 6-фтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  465. 6-fluorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
466. 6-xлop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  466. 6-chlorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
467. 6,8-дифтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3-b]индoл  467. 6,8-difluoro-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b ] indole
468. 12-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил} -6,7,8,9, 10,1 l-reкcaгидpo-5H-7Д 1- эпиминoциклooктa[b]индoл  468. 12-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -6,7,8,9, 10,1 l-rehydro-5H-7D 1-epiminocyclooct [b] indole
469. 2,12-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-6,7, 8,9,10, l l-гeкcaгидpo-5H- 7,1 l-эпиминoциклooктa[b] индол  469. 2,12-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -6,7, 8,9,10, l l-hexahydro-5H-7,1 l-epiminocyclooct [b] indole
470. 11 -мeтил-5- {2-[4-(тpифтopмeтил)фeнил]этил } -5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  470. 11-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
471. l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 471. l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
472. l,2,3,8-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-feтpaгидpo-Ш-пиpидo[4,3-b]индoл472. l, 2,3,8-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
473. l,2,3,6-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл473. l, 2,3,6-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
474. 8-мeтoкcи-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 474. 8-methoxy-l, 2,3-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
475. 8-фтop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  475. 8-fluor-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
476. 8-xлop- 1 ,2,3 -тpимeтил-5 -(3 -фeнилпpoпил)-2 ,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол  476. 8-chlorop- 1, 2,3-trimethyl-5 - (3-phenylpropyl) -2, 3, 4,5-tetrahydropo-1 N-pyrido [4,3 - b] indole
477. 6-фтop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  477. 6-fluoro-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
36 36
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) ( SUBSTITUTE SHEET (RULE 26) (
478. 6-xлop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол  478. 6-chlorop-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
479. 2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 479. 2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
480. 2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл480. 2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
481. 2-бeнзил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл481. 2-benzyl-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
482. 2,3,7,9-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл482. 2,3,7,9-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
483. 2-этил-3,7,9-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 483. 2-ethyl-3,7,9-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
484. 2,3,8-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 484. 2,3,8-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
485. 2-этил-3,8-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 485. 2-ethyl-3,8-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
486. 8-этил-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  486. 8-ethyl-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
487. 2,8-диэтил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  487. 2,8-diethyl-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
488. 2,3,6,9-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 488. 2,3,6,9-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
489. 2-этил-3,6,9-тpимeтил-5-(3-фeнилпpθпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 489. 2-ethyl-3,6,9-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
490. 2,3,6-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтp^гидpo-lH-пиpидo[4,3-b]индoл 490. 2,3,6-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetra ^ hydro-lH-pyrido [4,3-b] indole
491. 2-этил-3,6-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 491. 2-ethyl-3,6-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
492. 8-мeтoкcи-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  492. 8-methoxy-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
493. 2-этил-8-мeтoкcи-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  493. 2-ethyl-8-methoxy-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
494. 8-фтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  494. 8-fluoro-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
495. 2-этил-8-фтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  495. 2-ethyl-8-fluoro-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
496. 8-xлop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5^тeтpaгидpo-lH-пиpидo[4,3- b] индол 496. 8-chlorop-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5 ^ tetrahydro-lH-pyrido [4,3-b] indole
497. 8-xлop-2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  497. 8-chlorop-2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
498. 6-фтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  498. 6-fluoro-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
37 37
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 499. 2-этил-6-фтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол _ SUBSTITUTE SHEET (RULE 26) 499. 2-ethyl-6-fluoro-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole _
500. 6-xлop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  500. 6-chlorop-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
501. 6-xлop-2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  501. 6-chlorop-2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
502. 6,8-дифтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  502. 6,8-difluoro-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
503. 2-этил-6,8-дифтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  503. 2-ethyl-6,8-difop-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
504. 6-фтop-2,3,9-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  504. 6-fluoro-2,3,9-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
505. 2-этил-6-фтop-3,9-димeтил-5-(3-фeнилпpoпилЯ2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  505. 2-ethyl-6-fluoro-3,9-dimethyl-5- (3-phenylpropyl2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
506. l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 506. l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
507. l,2,8-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл507. l, 2,8-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
508. 8-этил-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 508. 8-ethyl-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
509. l,2,6-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 509. l, 2,6-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
510. 8-мeтoкcи-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 510. 8-methoxy-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
511. 8-фтop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  511. 8-fluorop-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
512. 8-xлop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  512. 8-chlorop-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
513. 6-фтop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  513. 6-fluorop-l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
514. 6-xлop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  514. 6-chlorop-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
515. 6,8-дифтop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  515. 6,8-diptop-l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
516. l,2-димeтил-8-(мeтилcyльфoнил)-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  516. l, 2-dimethyl-8- (methylcylphonyl) -5- (3-phenylpropyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
517. 12-мeтил-5-(3-фeншшpoпил)-6,7,8,9,10,ll-гeкcaгидpo-5H-7,l1- эпиминoциклooктa[b]индол  517. 12-methyl-5- (3-phenyl) -6,7,8,9,10, ll-hexahydro-5H-7, l1-epiminocyclooct [b] indole
38 38
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 518. 2,12-димeтил-5-(3-фeнилпpoпил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл SUBSTITUTE SHEET (RULE 26) 518. 2,12-dimethyl-5- (3-phenyl-propyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
519. 11 -мeтил-5-(3-фeнилпpoпил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  519. 11-methyl-5- (3-phenyl-propyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
520. 2,11 -димeтил-5-(3-фeнилпpoпил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  520. 2,11-dimethyl-5- (3-phenyl-propyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
521. 2-мeтoкcи-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7Д0- эпиминoциклoгeптa[b]индoл  521. 2-methoxy-l l-methyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7D0-epiminocyclohepta [b] indole
522. 2-фтop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  522. 2-fluorop-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [b] indole
523. 2-xлop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7Д0- эпиминoциклoгeптa[b] индол  523. 2-chlorop-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7D0-epiminocyclohepta [b] indole
524. l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  524. l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
525. l,2,3,8-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  525. l, 2,3,8-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
526. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  526. l, 2,3,6-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
527. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3 -b] индол  527. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
528. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  528. 8-fluor-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
529. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  529. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
530. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  530. 6-fluorop-l, 2,3-trimethyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
531. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)s2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  531. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) s2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
532. 2,3 -димeтил-5 -(2-пиpидин-2-илэтил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b]индoл 532. 2,3-dimethyl-5 - (2-pyridin-2-yl-ethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
533. 2-этил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 533. 2-ethyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
534. 2-бeнзил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  534. 2-benzyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
535. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  535. 2,3,7,9-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
39 39
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 536. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол SUBSTITUTE SHEET (RULE 26) 536. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
537. 2,3,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  537. 2,3,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
538. 2-этил-3,8-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  538. 2-ethyl-3,8-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
539. 8-этил-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  539. 8-ethyl-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
540. 2,8-диэтил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  540. 2,8-diethyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
541. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,ЗД5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  541. 2,3,6,9-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2, ZD5-tetrahydro-lH-pyrido [4,3-b] indole
542. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  542. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
543. 2,3,6-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  543. 2,3,6-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
544. 2-этил-3,6-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  544. 2-ethyl-3,6-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
545. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  545. 8-methoxy-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
546. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  546. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
547. 8-фтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  547. 8-fluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
548. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  548. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
549. 8-xлop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  549. 8-chlorop-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
550. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  550. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
551. 8-бpoм-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  551. 8-bromo-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
552. 6-фтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  552. 6-fluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
40 40
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 553. 2-этил-6-фтop-3-мeтил-5~(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 553. 2-ethyl-6-fluoro-3-methyl-5 ~ (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
554. 6-xлop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  554. 6-chlorop-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
555. 6-xлop-2-этил-3 -мeтил-5 -(2-пиpидин-2-илэтил)-2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол  555. 6-chlorop-2-ethyl-3-methyl-5 - (2-pyridin-2-yl-ethyl) -2,3, 4,5-tetrahydro-1 N-pyrido [4,3 - b] indole
556. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  556. 6,8-difluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
557. 2-этил-6,8-дифтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтparидpo-Ш- пиридо [4,3 -bjиндол  557. 2-ethyl-6,8-difop-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetraparidro-Ш-pyrido [4,3-bjindole
558. 6-фтop-2,3,9-тpимeтил-5-(2-пиpидинr2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 558. 6-fluoro-2,3,9-trimethyl-5- (2-pyridine r 2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
559. 2-этил-6-фтop-3,9-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  559. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
560. l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 560. l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
561. l,2,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 561. l, 2,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
562. 8-этил-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  562. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
563. l,2,6-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  563. l, 2,6-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
564. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индол  564. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
565. 8-этoкcи-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  565. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
566. 8-фтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b]индол  566. 8-fluorop-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
567. 8-xлop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  567. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
568. 8-бpoм-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  568. 8-bromo-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
569. 6-фтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  569. 6-fluoro-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
570. 6-xлop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  570. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
41 41
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 571. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл SUBSTITUTE SHEET (RULE 26) 571. 6,8-difluoro-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
572. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пири до [4 ,3 -b] индол  572. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-Shpiri to [4, 3-b] indole
573. 12-мeтил-5-(2-пиpидин-2-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  573. 12-methyl-5- (2-pyridin-2-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
574. 2,12-димeтил-5-(2-пиpидин-2-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  574. 2,12-dimethyl-5- (2-pyridin-2-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
575. l l-мeтил-5-(2-пиpидин-2-илэтил)-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  575. l l-methyl-5- (2-pyridin-2-yl-ethyl) -5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
576. 2,l l-димeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  576. 2, l l-dimethyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
577. 2-мeтoкcи-l l-мeтил-5-(2-пиpидин-2-илэтил)-5,6,7, 8,9,10-гeкcarидpo-7, 10- эпиминoциклoгeптa[b]индoл  577. 2-methoxy-l l-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7, 8,9,10-hexcaridpo-7, 10-epiminocyclohepta [b] indole
578. 2-фтop-l l-мeтил-5-(2-пиpидин-2-илэ,тил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  578. 2-fluorop-l l-methyl-5- (2-pyridin-2-yl, tyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
579. 2-xлop- 11 -мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  579. 2-chloro-11-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
580. l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  580. l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
581. 1,2,3, 8-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2, 3,4,5-тeтpaгидpo-l H-пиpидo[4,3- b] индол  581. 1,2,3, 8-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2, 3,4,5-tetrahydro-l H-pyrido [4,3-b] indole
582. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  582. l, 2,3,6-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
583. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  583. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-Ш-pyrido [4,3 -b] indole
584. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  584. 8-fluorop-l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
585. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  585. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
586. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  586. 6-fluoro-l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
587. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  587. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
588. 2,3 -димeтил-5 -(2-пиpидин-З -илэтил)-2,3 ,4,5 -τетрагидро- 1 Н-пиридо [4,3 -b] индол  588. 2,3-dimethyl-5 - (2-pyridine-3-ethylethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
42 42
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 589. 2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол SUBSTITUTE SHEET (RULE 26) 589. 2-ethyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
590. 2-бeнзил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  590. 2-benzyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
591. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  591. 2,3,7,9-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
592. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  592. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
593. 2,3,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  593. 2,3,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
594. 2-этил-3,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  594. 2-ethyl-3,8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
595. 8-этил-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  595. 8-ethyl-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
596. 2,8-диэтил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  596. 2,8-diethyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
597. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  597. 2,3,6,9-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
598. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  598. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
599. 2,3,6-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  599. 2,3,6-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
600. 2-этил-3,6-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  600. 2-ethyl-3,6-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
601. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  601. 8-methoxy-2,3-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
602. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  602. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
603. 8-фтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  603. 8-fluoro-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
604. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  604. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
605. 8-xлop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  605. 8-chlorop-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
43 43
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 606. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 606. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
607. 8-бpoм-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  607. 8-bromo-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
608. 6-фтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  608. 6-fluoro-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
609. 2-этил-6-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  609. 2-ethyl-6-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
610. 6-xлop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  610. 6-chlorop-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
611. 6-xлop-2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  611. 6-chlorop-2-ethyl-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
612. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  612. 6,8-difert-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
613. 2-этил-6,8-дифтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  613. 2-ethyl-6,8-difop-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
614. 6-фтop-2,3,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  614. 6-fluoro-2,3,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
615. 2-этил-6-фтop-3,9-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  615. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
616. l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 616. l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
617. l,2,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 617. l, 2,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
618. 8-этил-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  618. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
619. l,2,6-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  619. l, 2,6-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
620. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  620. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
621. 8-этoкcи-l ,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  621. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
622. 8-фтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  622. 8-fluoro-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
623. 8-xлop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  623. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
44 44
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 624. 8-бpoм-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 624. 8-bromo-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
625. 6-фтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  625. 6-fluorop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
626. 6-xлop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  626. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
627. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  627. 6,8-diptop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
628. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  628. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
629. 12-мeтил-5-(2-пиpидин-3-илэтил)-6,7, 8,9,10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  629. 12-methyl-5- (2-pyridin-3-yl-ethyl) -6,7, 8,9,10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
630. 2Д 2-димeтил-5-(2-пиpидин-3-илэтил)-6,7, 8,9,1 ОД l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  630. 2D 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -6.7, 8.9.1 OD l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
631. 1 l-мeтил-5-(2-пиpидин-3-илэтил)-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  631. 1 l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
632. 2,l l-димeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  632. 2, l l-dimethyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
633. 2-мeтoкcи-l l-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  633. 2-methoxy-l l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
634. 2-фтop-l l-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9Д0-гeкcaгидpo-7Д0- эпиминoциклoгeптa[b] индол  634. 2-fluorop-l l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9D0-hexahydro-7D0-epiminocyclohepta [b] indole
635. 2-xлop- 11 -мeтил-5-(2-пиpидин-3-илэтил)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  635. 2-chloro-11-methyl-5- (2-pyridin-3-yl-ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
636. l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  636. l, 2,3-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
637. l,2,3,8-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  637. l, 2,3,8-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
638. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  638. l, 2,3,6-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
639. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  639. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
640. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  640. 8-fluoro-l, 2,3-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
45 45
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 641. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 641. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
642. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  642. 6-fluorop-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
643. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  643. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
644. 2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 644. 2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
645. 2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 645. 2-ethyl-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
646. 2-бeнзил-3-мeтил-5-(2-пиpидин-4-илзтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  646. 2-benzyl-3-methyl-5- (2-pyridin-4-ylsyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
647. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  647. 2,3,7,9-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
648. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  648. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
649. 2,3,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол  649. 2,3,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
650. 2-этил-3,8-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  650. 2-ethyl-3,8-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
651. 8-этил-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  651. 8-ethyl-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
652. 2,8-диэтил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  652. 2,8-diethyl-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
653. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  653. 2,3,6,9-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
654. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  654. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
655. 2,3,6-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  655. 2,3,6-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
656. 2-этил-3,6-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  656. 2-ethyl-3,6-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
657. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  657. 8-methoxy-2,3-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
658. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  658. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4, 3-b] indole
46 46
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 659. 8-этoкcи-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 659. 8-ethoxy-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
660. 8-фтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  660. 8-fluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
661. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  661. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
662. 8-xлop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  662. 8-chlorop-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
663. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  663. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
664. 8-бpoм-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  664. 8-bromo-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
665. 6-фтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  665. 6-fluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
666. 2-этил-6-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  666. 2-ethyl-6-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
667. 6-xлop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  667. 6-chlorop-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
668. 6-xлop-2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  668. 6-chlorop-2-ethyl-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
669. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  669. 6,8-difluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
670. 6-фтop-2,3,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  670. 6-fluoro-2,3,9-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
671. l,2-димeтил-5-(2-пиpидин-4-илэтил)*-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл671. l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) * -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
672. l,2,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 672. l, 2,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
673. 8-этил-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  673. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
674. l,2,6-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  674. l, 2,6-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
675. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  675. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
676. 8-этoкcи-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  676. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
47 47
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 677. 8-фтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 677. 8-fluorop-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
678. 8-xлop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  678. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
679. 8-бpoм-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  679. 8-bromo-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
680. 6-фтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  680. 6-fluoro-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
681. 6-xлop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  681. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
682. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  682. 6,8-diptop-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
683. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  683. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-Ш-pyrido [4, 3-b] indole
684. 12-мeтил-5-(2-пиpидин-4-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  684. 12-methyl-5- (2-pyridin-4-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
685. 2,12-димeтил-5-(2-пиpидин-4-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  685. 2,12-dimethyl-5- (2-pyridin-4-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
686. l l-мeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  686. l l-methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
687. 2,11 -димeтил-5-(2-пиpидин-4-илэтил)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  687. 2,11-dimethyl-5- (2-pyridin-4-yl-ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
688. 2-мeтoкcи- 1 1 -мeтил-5-(2-пиpидин-4-илэтил)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  688. 2-methoxy-1 1-methyl-5- (2-pyridin-4-yl-ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
689. 2-фтop- 11 -мeтил-5-(2-пиpидин-4-илэтил)-5 ,6,7,8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  689. 2-fluoro-11-methyl-5- (2-pyridin-4-yl-ethyl) -5, 6,7,8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
690. 2-xлop- 11 -мeтил-5-(2-пиpидин-4-илэтил)-5 ,6,7,8,9, 10-reкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  690. 2-chlorop-11-methyl-5- (2-pyridin-4-yl-ethyl) -5, 6,7,8,9, 10-rehydro-7, 10-epiminocyclohepta [b] indole
691. 2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  691. 2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
692. 2,3,7,9-тeтpaмeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  692. 2,3,7,9-tetramethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
693. 2,3,8-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  693. 2,3,8-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
48 48
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 694. 2,3,6,9-тeтpaмeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл SUBSTITUTE SHEET (RULE 26) 694. 2,3,6,9-tetramethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
695. 2,3,6-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  695. 2,3,6-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
696. 8-мeтoкcи-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  696. 8-methoxy-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
697. 8-фтop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  697. 8-fluoro-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
698. 8-xлop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтparидpo-Ш- пиpидo[4,3-b]индoл  698. 8-chlorop-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
699. 6-фтop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3 -b] индол  699. 6-fluoro-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
700. 6-xлop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  700. 6-chlorop-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
701. 6-фтop-2,3,9-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3-,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  701. 6-fluoro-2,3,9-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3-, 4,5-tetrahydro-III-pyrido [4,3- b] indole
702. l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  702. l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
703. l,2,8-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтparидpo-Ш- пиридо [4,3 -b]индoл  703. l, 2,8-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
704. 8-этил-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  704. 8-ethyl-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
705. l,2,6-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  705. l, 2,6-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
706. 8-мeтoкcи-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  706. 8-methoxy-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
707. 8-фтop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  707. 8-fluoro-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
708. 8-xлop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3-b] индол  708. 8-chlorop-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
709. 6-фтop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  709. 6-fluoro-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
710. 6-xлop- 1 ,2-димeтил-5- [2-(6-мeтилпиpидин-3 -ил)этил] -2,3 ,4, 5 -тетрагидро- 1 H- пиpидo[4,3-b]индoл  710. 6-chlorop- 1, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
49 49
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 711. 6,8-дифтop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол SUBSTITUTE SHEET (RULE 26) 711. 6,8-diptop-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Ш-pyrido [4,3-bjindole
712. l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-8-(мeтилcyльфoнил)-2, 3,4,5- тетрагидро- 1 Н-пиридо [4,3 -b] индол  712. l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -8- (methylcylphonyl) -2, 3,4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
713. 2,12-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  713. 2,12-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b ] indole
714. l l-мeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  714. l l-methyl-5- [2- (6-methylpyridin-3-yl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
715. 2,11 -димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  715. 2,11-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
716. 2-фтop- 11 -мeтил-5 -[2-(6-мeтилпиpидин-3 -ил)этил] -5 ,6,7, 8 ,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  716. 2-fluorop-11-methyl-5 - [2- (6-methylpyridin-3-yl) ethyl] -5, 6,7, 8, 9, 10-hexahydro-7, 10-epiminocycle [b] indole
717. l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 717. l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
718. l,2,3,8-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл718. l, 2,3,8-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
719. l,2,3,6-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл719. l, 2,3,6-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
720. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 720. 8-methoxy-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
721. 8-фтop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,Ф,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  721. 8-fluoro-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3, Ф, 5-tetrahydro-lH-pyrido [4,3-b] indole
722. 8-xлop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  722. 8-chlorop-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
723. 6-фтop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  723. 6-fluoro-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
724. 6-xлop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  724. 6-chlorop-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
725. 2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 725. 2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
726. 2,3,7,9-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл726. 2,3,7,9-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
727. 2,3,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл727. 2,3,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
728. 8-этил-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл728. 8-ethyl-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
729. 2,3,6,9-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл729. 2,3,6,9-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
730. 2,3,6-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл730. 2,3,6-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
731. 8-мeтoкcи-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 731. 8-methoxy-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
732. 8-фтop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 732. 8-fluoro-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
733. 8-xлop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 733. 8-chloro-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
5P 5P
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 734. 6-фтop-2,3-димeтил-5-(2-фeнoкcиэтшi)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoлSUBSTITUTE SHEET (RULE 26) 734. 6-fluoro-2,3-dimethyl-5- (2-phenoxyethi) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
735. 6-xлop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл735. 6-chlorop-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
736. 6,8-дифтop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,344,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 736. 6,8-difluoro-2,3-dimethyl-5- (2-phenoxyethyl) -2.3 4 4,5-tetrahydro-III-pyrido [4,3-b] indole
737. 6-фтop-2,3,9-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  737. 6-fluoro-2,3,9-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
738. l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 738. l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
739. l,2,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл739. l, 2,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
740. 8-этил-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл740. 8-ethyl-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
741. l,2,6-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл741. l, 2,6-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
742. 8-мeтoкcи-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 742. 8-methoxy-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
743. 8-фтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 743. 8-fluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
744. 8-xлop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл744. 8-chlorop-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
745. 6-фтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл745. 6-fluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
746. 6-xлop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл746. 6-chlorop-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
747. 6,8-дифтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 747. 6,8-difluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
748. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] индол  748. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
749. 12-мeтил-5-(2-фeнoкcиэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  749. 12-methyl-5- (2-phenoxyethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
750. 2,12-димeтил-5-(2-фeнoкcиэтил)-6,7,8,9, 10,11 -гeкcaгидpo-5H-7, 11 - эпиминoциклooктa[b] индол „  750. 2,12-dimethyl-5- (2-phenoxyethyl) -6,7,8,9, 10,11-hexahydro-5H-7, 11 - epiminocyclooct [b] indole „
751. l l-мeтил-5-(2-фeнoкcиэтил)-5, 6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  751. l l-methyl-5- (2-phenoxyethyl) -5, 6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
752. 2,11 -димeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  752. 2,11-dimethyl-5- (2-phenoxyethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
753. 2-мeтoкcи- 11 -мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  753. 2-methoxy-11-methyl-5- (2-phenoxyethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
754. 2-фтop-l l-мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  754. 2-fluorop-l l-methyl-5- (2-phenoxyethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [b] indole
755. 2-xлop-l l-мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9,10-гeкcarидpo-7,10- эпиминoциклoгeптa[b]индoл  755. 2-chlorop-l l-methyl-5- (2-phenoxyethyl) -5,6,7,8,9,10-hexcaridro-7,10-epiminocyclohepta [b] indole
51 51
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) _ SUBSTITUTE SHEET (RULE 26) _
756. 5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  756. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
757. 5-[2-(3-фтopфeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  757. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
758. 5-[2-(3-фтopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  758. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
759. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтparидpo-Ш- пиридо [4,3 -b]индoл  759. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetra-para-III-pyrido [4,3 -b] indole
760. 8-фтop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  760. 8-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
761. 8-xлop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]ин дол  761. 8-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] in dol
762. 6-фтop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  762. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
763. 6-xлop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  763. 6-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
764. 5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 764. 5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
765. 5-[2-(3-фтopфeнил)этил]-2,3,7,9-тeтpaмeтил-2,5,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 765. 5- [2- (3-fluorophenyl) ethyl] -2,3,7,9-tetramethyl-2,5,4,5-tetrahydro-III-pyrido [4,3-b] indole
766. 5-[2-(3-фтopфeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  766. 5- [2- (3-fluorophenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
767. 8-этил-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  767. 8-ethyl-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
768. 5-[2-(3-фтopфeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  768. 5- [2- (3-fluorophenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
769. 5-[2-(3-фтopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  769. 5- [2- (3-fluorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
770. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-2,3-димeтцд-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  770. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-2,3-dimethcd-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
771. 8-фтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  771. 8-fluoro-5- [2- (3-fluoro-phenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
772. 8-xлop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  772. 8-chlorop-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
773. 6-фтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  773. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
52 52
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 774. 6-xлop-5- [2-(3 -фтopфeнил)этил] -2,3 -димeтил-2~3 ,4,5 -тетрагидро- 1 Н-пири до [4,3 - b]индoл SUBSTITUTE SHEET (RULE 26) 774. 6-chlorop-5- [2- (3-ketophenyl) ethyl] -2,3-dimethyl-2 ~ 3, 4,5-tetrahydro-1 H-pyri to [4,3 - b] indole
775. 6,8-дифтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  775. 6,8-diptop-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
776. 6-фтop-5-[2-(3-фтopфeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  776. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
777. 5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 777. 5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
778. 5-[2-(3-фтopфeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 778. 5- [2- (3-fluorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
779. 8-этил-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  779. 8-ethyl-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
780. 5-[2-(3-фтopфeнил)этил]-l,2,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  780. 5- [2- (3-fluorophenyl) ethyl] -l, 2,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
781. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  781. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
782. 8-фтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  782. 8-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
783. 8-xлop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  783. 8-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
784. 6-фтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  784. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
785. 6-xлop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2~3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  785. 6-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2 ~ 3,4,5-tetrahydro-III-pyrido [4,3-b] indole
786. 6,8-дифтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пири до [4 , 3 -b] индол  786. 6,8-difop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Shpiri to [4, 3-b] indole
787. 5-[2-(3-фтopфeнил)этил]-l,2-димeтил-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  787. 5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-8- (methylcylphonyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
788. 5-[2-(3-фтopфeнил)этил]-12-мeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  788. 5- [2- (3-fluorophenyl) ethyl] -12-methyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
789. 5-[2-(3-фтopфeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  789. 5- [2- (3-fluorophenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
790. 5-[2-(3-фтopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-jeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  790. 5- [2- (3-fluorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-jeccahydro-7,10-epiminocyclohepta [b] indole
791. 5-[2-(3-фтopфeнил)этил]-2,l l-димeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  791. 5- [2- (3-fluorophenyl) ethyl] -2, l l-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
53 53
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 792. 5-[2-(3-фтopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол SUBSTITUTE SHEET (RULE 26) 792. 5- [2- (3-fluorophenyl) ethyl] -2-methoxy-l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
793. 2-фтop-5-[2-(3-фтopфeнил)этил]-l l-мeтил-5, 6,7,8,9,10-reкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  793. 2-fluorop-5- [2- (3-fluorophenyl) ethyl] -l l-methyl-5, 6,7,8,9,10-reccahydro-7, 10-epiminocyclohepta [b] indole
794. 2-xлop-5-[2-(3-фтopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  794. 2-chlorop-5- [2- (3-fluorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-reccahydro-7,10-epiminocyclohepta [b] indole
795. 2-циклoгeкcил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  795. 2-cyclohexyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
796. 2-изoпpoпил-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcarидpo-7,10- эпиминoциклoгenтa[ό] индол  796. 2-isopropyl-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexcaridpo-7,10-epiminocyclogen [ό] indole
797. 2,4-дифтop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcarидpo-7,10- эпиминoциклoгeптa[6]индoл  797. 2,4-difluctop-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexcaridro-7,10-epiminocyclogen [6] indole
798. l-xлop-4,1 l-димeтил-5-(3-фeнилпpoпил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό]индoл  798. l-chlorop-4,1 l-dimethyl-5- (3-phenyl-propyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [ό] indole
799. 4-фтop-l,l l-димeтил-5-(3-фeнилпpoпил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό]индoл  799. 4-ftop-l, l l-dimethyl-5- (3-phenyl-propyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [ό] indole
800. 2,4,1 l-тpимeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[Ь]индoл  800. 2,4,1 l-trimethyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogene [b] indole
801. 2-этил- 11 -мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[Ь] индол  801. 2-ethyl-11-methyl-5- (3-phenyl-propyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
802. l l-циклoгeкcил-5-(3-фeнилпpoпил)-5 ,6,7,8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  802. l l-cyclohexyl-5- (3-phenyl-propyl) -5, 6,7,8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
803. 11 -бeнзил-5-(3-фeнилпpoпил)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[Ь]индoл  803. 11-benzyl-5- (3-phenyl-propyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
804. 2-мeтoкcи-l l-мeтил-5-(2-фeнилэтoкcи)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[Z?]индoл  804. 2-methoxy-l l-methyl-5- (2-phenylethoxy) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [Z?] Indole
805. 2-фтop-l l-мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9,10-гeкcaгидpo-'6,9- эпиминoциклoгeптa[6]индoл  805. 2-fluorop-l-methyl-5- (2-phenoxyethyl) -5,6,7,8,9,10-hexahydro-'6,9-epiminocyclohepta [6] indole
806. 2,3,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-ό]индoл 806. 2,3,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-ό] indole
807. 2-мeтил- 11 -мeтил-5-(2-фeнилэтoкcи)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[&] индол 807. 2-methyl-11-methyl-5- (2-phenylethoxy) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocycle [&] indole
808. 11 -мeтил-5-(2-фeнилэтoкcи)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[Z»]индoл  808. 11-methyl-5- (2-phenylethoxy) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocycle [Z ”] indole
809. 2-изoпpoпил- 11 -мeтил-5-(2-фeнилэтил)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[i»]индoл  809. 2-isopropyl-11-methyl-5- (2-phenylethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [i ”] indole
54 54
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 810. 11 -мeтил-2-этил-5-(2-фeнилэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол SUBSTITUTE SHEET (RULE 26) 810. 11-methyl-2-ethyl-5- (2-phenylethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
811. 1 l-циклoгeкcил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл  811. 1 l-cyclohexyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole
812. 11 -бeнзил-5-(2-фeнилэтил)-5, 6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол  812. 11-benzyl-5- (2-phenylethyl) -5, 6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [ό] indole
813. 2,11 -димeтил-5-(2-(4-мeтилфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[Z>] индол  813. 2,11-dimethyl-5- (2- (4-methylphenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [Z>] indole
814. 2,1 l-димeтил-5-(2-(2-мeтилфeнил)этил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό]индoл  814. 2,1 l-dimethyl-5- (2- (2-methylphenyl) ethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [ό] indole
815. 2,l l-димeтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9,10-гeкcarидpo-7,10- эпиминoциклoгeптa[ό] индол  815. 2, l l-dimethyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9,10-hexcaridpo-7,10-epiminocyclogen [ό] indole
816. 2Д l-димeтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол  816. 2D l-dimethyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
817. 11 -мeтил-5-(2-(4-мeтилфeнил)этил)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол  817. 11-methyl-5- (2- (4-methylphenyl) ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
818. l l-мeтил-5-(2-(2-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό]индoл  818. l l-methyl-5- (2- (2-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
819. 11 -Meтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[δ] индол  819. 11-Methyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocycle [δ] indole
820. 11 -мeтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[6] индол  820. 11-methyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [6] indole
821. l-этил-2-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 821. l-ethyl-2-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
822. 2-мeтил-3-этил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл822. 2-methyl-3-ethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
823. l-этил-2,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл823. l-ethyl-2,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
824. 2,8-димeтил-3-этил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл824. 2,8-Dimethyl-3-ethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
825. l,2-димeтил-5-(2-(2-фтopфeнил)этил^-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл825. l, 2-dimethyl-5- (2- (2-fluorophenyl) ethyl ^ -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
826. l,2,8-тpимeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл826. l, 2,8-trimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
827. 2,3-димeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл827. 2,3-dimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
828. 2,3,8-тpимeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл828. 2,3,8-trimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
829. l,2,3-тpимeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 829. l, 2,3-trimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
830. l,2,3,8-тeтpaмeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  830. l, 2,3,8-tetramethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
55 55
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 831. l,2-димeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 831. l, 2-dimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
832. l,2,8-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  832. l, 2,8-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
833. 2,3-димeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  833. 2,3-dimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
834. 2,3,8-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  834. 2,3,8-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
835. l,2,3-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  835. l, 2,3-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
836. l,2,3,8-тeтpaмeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  836. l, 2,3,8-tetramethyl-5- (2- (2,4-diferephenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
837. l ,2-димeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 837. l, 2-dimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
838. l,2,8-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл838. l, 2,8-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
839. 2,3-димeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл839. 2,3-dimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
840. 2,3,8-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл840. 2,3,8-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
841. 1 ,2,3-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл841. 1, 2,3-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
842. l,2,3,8-тeтpaмeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл842. l, 2,3,8-tetramethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
843. l,2-димeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл843. l, 2-dimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
844. l,2,8-тpимeтил-5-(2-(l-нaфтил)этил)-2,3^4,5-тeтparидpo-Ш-пиpидo[4,3-b]индoл844. l, 2,8-trimethyl-5- (2- (l-naphthyl) ethyl) -2,3 ^ 4,5-tetra-para-III-pyrido [4,3-b] indole
845. 2,3-димeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл845. 2,3-dimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
846. 2,3,8-тpимeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл846. 2,3,8-trimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
847. l,2,3-тpимeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл847. l, 2,3-trimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
848. l,2,3,8-тeтpaмeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл848. l, 2,3,8-tetramethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
849. (1 R)- 1 ,2-димeтил-5 -(2-фeнилэтил)-2,3 ,4,5 -тетрагидро- 1 H-пиpидo[4,3 -b] индол849. (1 R) - 1, 2-dimethyl-5 - (2-phenylethyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
850. (lS)-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл850. (lS) -l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
851. (IR)-1, 2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл851. (IR) -1, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
852. (lS)-l,2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл852. (lS) -l, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
853. (ЗR)-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл853. (3R) -2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
854. (ЗS)-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл854. (3S) -2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
855. (ЗR)-2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3~,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл855. (3R) -2,3,8-trimethyl-5- (2-phenylethyl) -2.3 ~, 4,5-tetrahydro-lH-pyrido [4,3-b] indole
856. (ЗS)-2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл856. (3S) -2,3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
857. (lR,ЗR)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 857. (lR, 3R) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
56 56
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 858. (lR,ЗS)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол SUBSTITUTE SHEET (RULE 26) 858. (lR, ZS) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
859. (lS,ЗR)-l,2,3-тpимeтил-5-(2-фeнилэтЪл)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  859. (lS, 3R) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
860. (lS,ЗS)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5гтeтpaгидpo-Ш-пиpидo[4,3- b] индол  860. (lS, ZS) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5tetrahydro-W-pyrido [4,3-b] indole
861. (lR,ЗR)-l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  861. (lR, 3R) -l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
862. (1R,ЗS)- 1,2,3, 8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4, 3- b] индол  862. (1R, ZS) - 1,2,3, 8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-W-pyrido [4, 3-b] indole
863. (lS,ЗR)-l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  863. (lS, 3R) -l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
864. (1S,ЗS)- 1,2,3, 8-тeтpaмeтил-5-(2-фeнилэтил)-2, 3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3- b] индол.  864. (1S, ZS) -1,2,3, 8-tetramethyl-5- (2-phenylethyl) -2, 3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole.
Следующим объектом, составляющим настоящее изобретение, является предложенные авторами соединения общей формулы I, обладающие физиологической активностью, а именно, нейропротекторными свойствами и свойством эффективно стимулировать когнитивные функции, что позволяет использовать их в качестве лекарственных субстанций, композиций и препаратов для людей и теплокровных животных, предназначенных для лечения нейродегенеративных болезней.  The next object constituting the present invention is the compounds of the general formula I proposed by the authors, having physiological activity, namely, neuroprotective properties and the ability to effectively stimulate cognitive functions, which allows them to be used as medicinal substances, compositions and preparations for humans and warm-blooded animals intended for the treatment of neurodegenerative diseases.
Следующим объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, проявляющие свойства антагонистов серотониновых рецепторов 5-HT6.  The next object that makes up the present invention, are physiologically active substances of the General formula I, showing the properties of antagonists of serotonin receptors 5-HT6.
Следующим объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, проявляющие свойства антагонистов серотониновых рецепторов 5-HT7.  The next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of 5-HT7 antagonists of serotonin receptors.
Следующим объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, проявляющие свойства ингибиторов бутирилхолинэстеразы BChE.  The next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of BChE butyrylcholinesterase inhibitors.
Следующим объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, проявляющие свойства эффекторов митохондриальных пор MPTP.  The next object constituting the present invention are physiologically active substances of the general formula I, exhibiting the properties of MPTP mitochondrial pore effectors.
Следующим предпочтительным объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, одновременно  The next preferred object constituting the present invention are physiologically active substances of General formula I, at the same time
57 57
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) проявляющие свойства антагонистов серотониновых рецепторов и ингибиторов бутирил холинэстеразы BChE. SUBSTITUTE SHEET (RULE 26) exhibiting the properties of serotonin receptor antagonists and butyryl cholinesterase BChE inhibitors.
Следующим предпочтительным объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, одновременно проявляющие свойства антагонистов серотониновых рецепторов и эффекторов митохондриальных пор MPTP.  The next preferred object constituting the present invention are physiologically active substances of the general formula I, simultaneously exhibiting the properties of antagonists of serotonin receptors and effectors of mitochondrial pores MPTP.
Следующим наиболее предпочтительным объектом, составляющим настоящее изобретение, являются физиологически активные вещества общей формулы I, одновременно проявляющие свойства антагонистов серотониновых рецепторов, ингибиторов бутирилхолинэстеразы BChE и эффекторов митохондриальных пор MPTP.  The next most preferred object constituting the present invention are physiologically active substances of the general formula I, which simultaneously exhibit the properties of serotonin receptor antagonists, BChE butyrylcholinesterase inhibitors and MPTP mitochondrial pore effectors.
Следующим объектом, составляющим данное изобретение, являются лекарственные субстанции на основе соединений общей формулы I для производства лекарственных препаратов и фармацевтических композиций.  The next object constituting this invention are medicinal substances based on compounds of the general formula I for the manufacture of pharmaceutical preparations and pharmaceutical compositions.
Следующим объектом, составляющим настоящее изобретение, являются разработанные авторами новые фармацевтические композиции, обладающие нейропротекторными свойствами, а также свойством эффективно воздействовать на когнитивные функции, содержащие указанные выше лекарственные субстанции, для использования в медицине и ветеринарии. Предложенные композиции в качестве активной субстанции содержат фармацевтически эффективное количество соединений, представленных формулами 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2. Понятие ((эффективное количеством используемое в данной заявке, подразумевает использование такого количества соединения формулы I, которое в соединение с его показателями активности и токсичности должно быть эффективным в данной лекарственной форме.  The next object that makes up the present invention are the new pharmaceutical compositions developed by the authors with neuroprotective properties, as well as the ability to effectively influence cognitive functions containing the above medicinal substances for use in medicine and veterinary medicine. The proposed compositions as an active substance contain a pharmaceutically effective amount of compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2. 2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2. The term ((effective amount used in this application, means the use of such an amount of a compound of formula I, which in combination with its indicators of activity and toxicity should be effective in this dosage form.
Объектом, составляющим настоящее изобретение, являются также способы создания новых фармацевтических композиций, содержащих в качестве активной субстанции одно или несколько соединений, представленных формулами 1, 1-1, 1-2, 1-3, I- 4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2. Способы заключаются в смешивании физиологически эффективного количества активной субстанции с инертными по отношению к субстанции наполнителями и/или разбавителями с последующим таблетированием, гранулированием, капсулированием, суспендированием, растворением или разбавлением и помещением в пригодную упаковку. Отличительной особенностью способов является использование в качестве активной субстанции соединений, представленных формулами 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2.  The object of the present invention are also methods of creating new pharmaceutical compositions containing, as an active substance, one or more compounds represented by formulas 1, 1-1, 1-2, 1-3, I-4, 1-5, 1.1. 1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2. The methods consist in mixing a physiologically effective amount of the active substance with excipients and / or diluents inert with respect to the substance, followed by tableting, granulation, encapsulation, suspension, dissolution or dilution and placed in a suitable package. A distinctive feature of the methods is the use of compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2 as the active substance , 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Объектом, составляющим настоящее изобретение, являются также лекарственные препараты в виде таблеток, желатиновых капсул, пилюль, порошков, гранул, пероральных растворов или суспензий, сублингвальных и трансбуккальных форм, аэрозолей, имплантатов, местных, трансдермальных, подкожных, внутримышечных, внутривенных, интраназальных, внутриглазных или ректальные форм, помещенных в фармацевтически приемлемую упаковку, и включающие в свой состав лекарственную субстанцию или фармацевтическую композицию, содержащие одно или нескольких соединений, представленных формулами 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2, предназначенные для лечения и предупреждения нейродегенеративных заболеваний, в том числе БА. SUBSTITUTE SHEET (RULE 26) The object of the present invention is also medicines in the form of tablets, gelatine capsules, pills, powders, granules, oral solutions or suspensions, sublingual and buccal forms, aerosols, implants, local, transdermal, subcutaneous, intramuscular, intravenous, intranasal, intraocular or rectal forms, placed in a pharmaceutically acceptable package, and including in its composition a drug substance or pharmaceutical composition containing one or more compounds equations represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, Ll.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2, intended for the treatment and prevention of neurodegenerative diseases, including AD.
Объектом, составляющим настоящее изобретение, является также способ лечения и предупреждения нейродегенеративных заболеваний животных и людей патогенез которых связан с дисфункцией серотонинэргической и/или холинэргической систем, а также с нарушением функций митохондрий. Способ заключается в применении новых лекарственных препаратов, содержащих в качестве активной субстанции эффективное количество одного или нескольких соединений, представленных формулами 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2.  The object of the present invention is also a method for the treatment and prevention of neurodegenerative diseases of animals and humans whose pathogenesis is associated with dysfunction of the serotonergic and / or cholinergic systems, as well as with dysfunction of the mitochondria. The method consists in the use of new drugs containing as an active substance an effective amount of one or more compounds represented by formulas 1, 1-1, 1-2, 1-3, 1-4, 1-5, 1.1.1, 1.1. 2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2.
Следующим предпочтительным объектом, составляющим настоящее изобретение, является способ лечения и предупреждения нейродегенеративных заболеваний у человека или теплокровного животного, вкючающих болезни Альцгеймера и Паркинсона; болезнь (хорею) Хантингтона; рассеянный склероз; мозжечковую дегенерацию; амиотрофический латеральный склероз; деменцию с тельцами Леви; спинальную мускульную атрофию; периферическую нейропатию; губчатый энцефалит ' («кopoвьe бeшeнcтвo»); СПИД- ассоциированную деменцию; мультиинфарктную деменцию; лoбнo1виcoчнyю деменцию; лейкоэнцефалопатию; хронические нейродегенеративные заболевания; инсульт; ишемическое, реперфузионное и гипоксическое повреждения мозга; эпилепсию; церебральную ишемию; глаукому; черепно-мозговую травму; синдром Дауна; энцефаломиелит; менингит; энцефалит; нейробластому; шизофрению; депрессию, а также нейрональные повреждения, ассоциированные с аутоиммунными, инфекционными, онкологическими и эндокринными заболеваниями; и прочие нейродегенеративные процессы. The next preferred object constituting the present invention is a method for the treatment and prevention of neurodegenerative diseases in humans or warm-blooded animals, including Alzheimer's and Parkinson's;Huntington's disease (chorea); multiple sclerosis; cerebellar degeneration; amyotrophic lateral sclerosis; dementia with Levy bodies; spinal muscular atrophy; peripheral neuropathy; spongiform encephalitis ' (“bovine rabies”); AIDS-related dementia; multi-infarct dementia; Especially 1 acute dementia; leukoencephalopathy; chronic neurodegenerative diseases; stroke; ischemic, reperfusion, and hypoxic brain damage; epilepsy cerebral ischemia; glaucoma; traumatic brain injury; Down syndrome; encephalomyelitis; meningitis; encephalitis; neuroblastoma; schizophrenia; depression, as well as neuronal damage associated with autoimmune, infectious, oncological and endocrine diseases; and other neurodegenerative processes.
Следующим предпочтительным объектом, составляющим настоящее изобретение, является способ лечения и предупреждения нейродегенеративных процессов у человека или теплокровного животного, связанных со старением организма.  The next preferred object constituting the present invention is a method for the treatment and prevention of neurodegenerative processes in humans or warm-blooded animals associated with aging of the body.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Следующим предпочтительным объектом, составляющим настоящее изобретение, является способ лечения и предупреждения нейродегенеративных заболеваний путем введения человеку или теплокровному животному лекарственного средства в дозе 0,005 - 10.0 мг/кг массы тела по крайней мере один раз в день в течение периода, необходимого для достижения терапевтического эффекта. SUBSTITUTE SHEET (RULE 26) The next preferred object constituting the present invention is a method of treating and preventing neurodegenerative diseases by administering to a human or warm-blooded animal a drug at a dose of 0.005 to 10.0 mg / kg body weight at least once a day for a period necessary to achieve a therapeutic effect.
Следующим объектом, составляющим данное изобретение, являются соединения общей формулы I, обладающие свойством эффективно воздействовать на серотониновые рецепторы 5-HT6 и/или 5-HT7, и/или на бутирилхолинэстеразу BuChE и/или митохондрии, предназначенные для экспериментального исследования биохимических сигнальных систем и физиологических процессов iп vitrо и iп vivо в качестве ((фармакологических инструментов)).  The next object constituting this invention are compounds of general formula I, which have the property to effectively act on 5-HT6 and / or 5-HT7 serotonin receptors, and / or on BuChE butyrylcholinesterase and / or mitochondria, intended for experimental study of biochemical signal systems and physiological IP vitro and ip vivo processes as ((pharmacological instruments)).
Следующим объектом, составляющим настоящее изобретение, является разработанный авторами способ получения соединений, представленных формулой 1.1. Согласно настоящему изобретению соединения формулы 1.1 получают в соответствии со схемой 1.  The next object that makes up the present invention is a method developed by the authors for the preparation of compounds represented by formula 1.1. According to the present invention, the compounds of formula 1.1 are obtained in accordance with scheme 1.
Схема 1 Scheme 1
Figure imgf000062_0001
Figure imgf000062_0001
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
Для этого арилгидразин I. Ia в виде свободного основания или соли (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и "другие) смешивается с пиперидиноном I. Ib или его солью (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и другие) при температуре 0-1000C в воде, спиртах или других протонных или апротонных растворителях (HOAc, HOOCH, HOOC-AIk, ДМСО, ДМФА, метилпирролидон, ацетонитрил и другие, или в смеси этих растворителей) при перемешивании или без перемешивании. После этого к смеси добавляется кислота (HCl, HBr, HI, H2SO4, HOSO2R, HЗPO4, полифосфорная кислота, PC13, ВFЗ и другие) и реакция проводится при перемешивании (или без), при температуре 0-2000C, с микроволновым облучением (или без), с ультразвуковым облучением (или без) до тех пор, пока не завершится образование индола I.lс. Время реакции составляет от 30 мин до 100 часов. После этого вещество I.lс выделяют и очищают, хроматографией или кристаллизуют. Затем производят алкилирование вещества I.lс. Для этого к раствору индола I.lс в ДМФА (или в другом For this, aryl hydrazine I. Ia in the form of a free base or salt (hydrochloride, hydrobromide, hydrosulfate, hydrogen phosphate and others) is mixed with piperidinone I. Ib or its salt (hydrochloride, hydrobromide, hydrosulfate, hydrogen phosphate and others) at a temperature of 0-100 0 C in water, alcohols or other protic or aprotic solvents (HOAc, HOOCH, HOOC-AIk, DMSO, DMF, methylpyrrolidone, acetonitrile and others, or a mixture of these solvents) with or without stirring. After this, acid (HCl) is added to the mixture. , HBr, HI, H2SO4, HOSO2R, HЗPO4, polyphosphoric acid, P C13, VFZ and others) and the reaction is carried out with stirring (or without), at a temperature of 0-200 0 C, with microwave irradiation (or without), with ultrasonic irradiation (or without) until the formation of indole I. lc. The reaction time is from 30 minutes to 100 hours. After that, the substance I.lc is isolated and purified by chromatography or crystallization. Then the alkylation of the substance I.lc is carried out. For this, to a solution of indole I.lc in DMF (or in another
60  60
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.) добавляют избыток (2-5 кратный) NaH при температуре реакционной смеси -70- 300C. Смесь выдерживают 30 минут - 1.5 часов при этой температуре, а затем быстро прибавляют раствор 2-3 -кратного избытка тозилата или бромида (хлорида, иодида, сульфоната) или алкена (стиролы, винилпиридины) в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.). Смесь перемешивают 1-18 часов при комнатной температуре или нагревают до 30-2500C. Реакционную смесь разлагают водой или кислотой. Целевое вещество экстрагируют этилацетатом или другим растворителем, сушат над поташом или другим осушителем и упаривают в вакууме или при нормальном давлении. Продукт 1.1 в виде основания или фармацевтически приемлимой соли очищают методом колоночной хроматографии и/или кристаллизуют. SUBSTITUTE SHEET (RULE 26) aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.) add an excess (2-5 times) of NaH at the temperature of the reaction mixture -70-30 0 C. The mixture is kept for 30 minutes - 1.5 hours at this temperature, and then quickly add a solution of 2-3-fold excess of tosylate or bromide (chloride, iodide, sulfonate) or alkene (styrene, vinylpyridines) in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.). The mixture is stirred for 1-18 hours at room temperature or heated to 30-250 0 C. The reaction mixture is decomposed with water or acid. The target substance is extracted with ethyl acetate or another solvent, dried over potash or other desiccant and evaporated in vacuo or under normal pressure. Product 1.1, in the form of a base or a pharmaceutically acceptable salt, is purified by column chromatography and / or crystallized.
Следующим объектом, составляющим настоящее изобретение, является разработанный авторами способ получения соединений, представленных формулой 1.2. Согласно настоящему изобретению соединения формулы 1.2 получают в соответствии со схемой 2.  The next object that makes up the present invention is a method developed by the authors for the preparation of compounds represented by formula 1.2. According to the present invention, the compounds of formula 1.2 are obtained in accordance with scheme 2.
Figure imgf000063_0001
Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0002
CH2CH2-Hal, CH=CH2, еtс. CH2CH2-Hal, CH = CH2, etc.
Figure imgf000063_0003
Figure imgf000063_0003
Для этого к раствору изотриптамина I.2a в инертном растворителе (толуоле, бензоле, ТГФ, диоксане и т.п.) прибавляют при перемешивании эквивалент или избыток свежеперегнанного альдегида I.2b в присутствии уксусной или другой кислоты. Время реакция составляет 5 - 24 часов. Затем растворители упаривают, остаток обрабатывают водой, подщелачивают и экстрагируют этилацетатом или другим растворителем. Экстракт сушат над поташом или другим осушителем и упаривают в вакууме или при нормальном давлении. Вещество I.2c очищают колоночной хроматографией. Затем производят алкилирование вещества I.2c. Для этого к раствору индола I.2c в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан,  For this, an equivalent or excess of freshly distilled aldehyde I.2b in the presence of acetic or other acid is added to a solution of isotriptamine I.2a in an inert solvent (toluene, benzene, THF, dioxane, etc.). The reaction time is 5-24 hours. Then the solvents are evaporated, the residue is treated with water, made basic and extracted with ethyl acetate or another solvent. The extract is dried over potash or other desiccant and evaporated in vacuo or at normal pressure. Substance I.2c was purified by column chromatography. Then the alkylation of substance I.2c is carried out. To do this, to a solution of indole I.2c in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane,
61  61
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) диглим, ацетонитрил и т.п.) добавляют избыток (2-5 кратный) NaH при температуре реакционной смеси -70- 3O0C. Смесь выдерживают 30 минут — 1.5 часов при этой температуре, а затем быстро прибавляют раствор 2-3 -кратного избытка тозилата или бромида (хлорида, иодида, сульфоната) или алкена (стиролы, винилпиридины) в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.). Смесь перемешивают 1-18 часов при комнатной температуре или нагревают до 30-2500C. Реакционную смесь разлагают водой или кислотой. Целевое вещество экстрагируют этилацетатом или другим растворителем, сушат над поташом или другим осушителем и упаривают в вакууме или при нормальном давлении. Продукт 1.2 в виде основания или фармацевтически приемлимой соли очищают методом колоночной хроматографии и/или кристаллизуют. SUBSTITUTE SHEET (RULE 26) diglyme, acetonitrile, etc.) add an excess (2-5-fold) of NaH at a temperature of the reaction mixture of -70-3O 0 C. The mixture is kept for 30 minutes - 1.5 hours at this temperature, and then a 2-3-fold solution is quickly added. excess tosylate or bromide (chloride, iodide, sulfonate) or alkene (styrene, vinyl pyridines) in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.) . The mixture is stirred for 1-18 hours at room temperature or heated to 30-250 0 C. The reaction mixture is decomposed with water or acid. The target substance is extracted with ethyl acetate or another solvent, dried over potash or other desiccant and evaporated in vacuo or under normal pressure. Product 1.2, in the form of a base or a pharmaceutically acceptable salt, is purified by column chromatography and / or crystallized.
Следующим объектом, составляющим настоящее изобретение, является разработанный авторами способ получения соединений, представленных формулой 1.3. Согласно настоящему изобретению соединения формулы 1.2 получают в соответствии со схемой 3.  The next object that makes up the present invention is a method developed by the authors for the preparation of compounds represented by formula 1.3. According to the present invention, the compounds of formula 1.2 are obtained in accordance with scheme 3.
Схема 3 Scheme 3
Figure imgf000064_0001
Figure imgf000064_0001
X = CH2CH2-Hal, CH=CH2, еtс
Figure imgf000064_0002
X = CH2CH2-Hal, CH = CH2, etc
Figure imgf000064_0002
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
Для этого арилгидразин I.За в виде свободного основания или соли (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и другие) смешивается с пиперидиноном I.Зb или его солью (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и другие) при температуре 0-1000C в воде, спиртах или других протонных или апротонных растворителях (HOAc, HOOCH, HOOC-AIk, ДМСО, ДМФА, метилпирролидон, ацетонитрил и другие, или в смеси этих растворителей) при перемешивании или без перемешивании. После этого к смеси добавляется кислота (HCl, HBr, HI, H2SO4, To do this, aryl hydrazine I. Behind in the form of a free base or salt (hydrochloride, hydrobromide, hydrosulfate, hydrophosphate and others) is mixed with piperidinone I.Zb or its salt (hydrochloride, hydrobromide, hydrosulfate, hydrophosphate and others) at a temperature of 0-100 0 C in water, alcohols or other protic or aprotic solvents (HOAc, HOOCH, HOOC-AIk, DMSO, DMF, methylpyrrolidone, acetonitrile and others, or a mixture of these solvents) with or without stirring. After this, acid (HCl, HBr, HI, H2SO4,
62 62
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) HOSO2R, HЗPO4, полифосфорная кислота, PC13, ВFЗ и другие) и реакция проводится при перемешивании (или без), при температуре 0-2000C, с микроволновым облучением (или без), с ультразвуковым облучением (или без) до тех пор, пока не завершится образование индола I.Зс. Время реакции составляет от ЗО'мин до 100 часов. После этого вещество I.3c выделяют и очищают, хроматографией или кристаллизуют. Затем производят алкилирование вещества I.Зс. Для этого к раствору индола I.Зс в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.) добавляют избыток (2-5 кратный) NaH при температуре реакционной смеси -70- 3O0C. Смесь выдерживают 30 минут - 1.5 часов при этой температуре, а затем быстро прибавляют раствор 2-3 -кратного избытка тозилата или бромида (хлорида, иодида, сульфоната) или алкена (стиролы, винилпиридины) в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.). Смесь перемешивают 1-18 часов при комнатной температуре или нагревают до 30-2500C. Реакционную смесь разлагают водой или кислотой. Целевое вещество экстрагируют этилацетатом или другим растворителем, сушат над поташом или другим осушителем и упаривают в вакууме или при нормальном давлении. Продукт 1.3 в виде основания или фармацевтически приемлимой соли очищают методом колоночной хроматографии и/или кристаллизуют. SUBSTITUTE SHEET (RULE 26) HOSO2R, HЗPO4, polyphosphoric acid, PC13, ВФЗ and others) and the reaction is carried out with stirring (or without), at a temperature of 0-200 0 C, with microwave radiation (or without), with ultrasonic radiation (or without) until until the formation of indole I.Z.s. The reaction time is from LP 'minutes to 100 hours. Subsequently, the I.3c material is isolated and purified by chromatography or crystallization. Then the alkylation of substance I.Z.s. For this, an excess (2-5-fold) of NaH is added to a solution of indole I. 3c in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.) the temperature of the reaction mixture is -70-3O 0 C. The mixture is kept for 30 minutes - 1.5 hours at this temperature, and then a solution of 2-3-fold excess of tosylate or bromide (chloride, iodide, sulfonate) or alkene (styrene, vinylpyridines) is quickly added to DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.). The mixture is stirred for 1-18 hours at room temperature or heated to 30-250 0 C. The reaction mixture is decomposed with water or acid. The target substance is extracted with ethyl acetate or another solvent, dried over potash or other desiccant and evaporated in vacuo or under normal pressure. Product 1.3, in the form of a base or a pharmaceutically acceptable salt, is purified by column chromatography and / or crystallized.
Следующим объектом, составляющим настоящее изобретение, является разработанный авторами способ получения соединений, представленных формулами 1.4 и 1.5. Согласно настоящему изобретению соединения формулы 1.4 и 1.5 получают в соответствии со схемой 4.  The next object that makes up the present invention is a method developed by the authors for the preparation of compounds represented by formulas 1.4 and 1.5. According to the present invention, the compounds of formula 1.4 and 1.5 are obtained in accordance with scheme 4.
Схема 4 ,2Scheme 4, 2
Figure imgf000065_0001
Figure imgf000065_0001
CH2CH2-Hal, CH=CH2, еtс  CH2CH2-Hal, CH = CH2, etc
Figure imgf000065_0002
Figure imgf000065_0002
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
63 63
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Для этого арилгидразин I.4-5a в виде свободного основания или соли (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и другие) смешивается с пиперидиноном I.4b или I.5b или их солями (гидрохлорид, гидробромид, гидросульфат, гидрофосфат и другие) при температуре 0-1000C в воде, спиртах или других протонных или апротонных растворителях (HOAc, HOOCH, HOOC-AIk, ДМСО, ДМФА, метилпирролидон, ацетонитрил и другие, или в смеси этих растворителей) при перемешивании или без перемешивании. После этого к смеси добавляется кислота (HCl, HBr, HI, H2SO4, HOSO2R, HЗPO4, полифосфорная кислота, PC13, ВFЗ и другие) и реакция проводится при перемешивании (или без), при температуре 0-2000C, с микроволновым облучением (или без), с ультразвуковым облучением (или без) до тех пор, пока не завершится образование индола I.4c или I.5c. Время реакции составляет от 30 мин до 100 часов. После этого вещество I.4c или I.5c выделяют и очищают, хроматографией или кристаллизуют. Затем производят алкилирование вещества L4c или I.5c. Для этого к раствору индола I.4c или I.5c в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.) добавляют избыток (2-5 кратный) NaH при температуре реакционной смеси -70- 3O0C. Смесь выдерживают 30 минут— 1.5 часов при этой температуре, а затем быстро прибавляют раствор 2-3 -кратного избытка тозилата или *бpoмидa (хлорида, иодида, сульфоната) или алкена (старо лы, винил пиридины) в ДМФА (или в другом апротонном растворителе: ДМСО, NMP, ТГФ, эфир, толуол, диоксан, диметоксиэтан, диглим, ацетонитрил и т.п.). Смесь перемешивают 1-18 часов при комнатной температуре или нагревают до 30-2500C. Реакционную смесь разлагают водой или кислотой. Целевое вещество экстрагируют этилацетатом или другим растворителем, сушат над поташом или другим осушителем и упаривают в вакууме или при нормальном давлении. Продукт 1.4 или 1.5 в виде основания или фармацевтически приемлимой соли очищают методом колоночной хроматографии и/или кристаллизуют. SUBSTITUTE SHEET (RULE 26) For this, aryl hydrazine I.4-5a in the form of a free base or salt (hydrochloride, hydrobromide, hydrosulfate, hydrogen phosphate and others) is mixed with piperidinone I.4b or I.5b or their salts (hydrochloride, hydrobromide, hydrosulfate, hydrogen phosphate and others) at temperature 0-100 0 C in water, alcohols or other protic or aprotic solvents (HOAc, HOOCH, HOOC-AIk, DMSO, DMF, methylpyrrolidone, acetonitrile and others, or in a mixture of these solvents) with or without stirring. After that, acid is added to the mixture (HCl, HBr, HI, H2SO4, HOSO2R, HЗPO4, polyphosphoric acid, PC13, ВФЗ and others) and the reaction is carried out with stirring (or without), at a temperature of 0-200 0 C, with microwave irradiation ( with or without), with ultrasonic irradiation (or without) until the formation of indole I.4c or I.5c is complete. The reaction time is from 30 minutes to 100 hours. Subsequently, the I.4c or I.5c material is isolated and purified by chromatography or crystallization. Then the alkylation of the substance L4c or I.5c is carried out. For this, an excess (2-5) is added to a solution of indole I.4c or I.5c in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile, etc.) multiple) NaH at a reaction mixture temperature of -70-3O 0 C. The mixture is held for 30 minutes — 1.5 hours at this temperature, and then a solution of 2-3-fold excess of tosylate or * bromide (chloride, iodide, sulfonate) or alkene ( old ly, vinyl pyridines) in DMF (or in another aprotic solvent: DMSO, NMP, THF, ether, toluene, dioxane, dimethoxyethane, diglyme, acetonitrile etc.). The mixture is stirred for 1-18 hours at room temperature or heated to 30-250 0 C. The reaction mixture is decomposed with water or acid. The target substance is extracted with ethyl acetate or another solvent, dried over potash or other desiccant and evaporated in vacuo or under normal pressure. Product 1.4 or 1.5 as a base or a pharmaceutically acceptable salt is purified by column chromatography and / or crystallized.
Ниже изобретение описывается с помощью примеров, которые иллюстрируют, но не ограничивают данное изобретение.  The invention is described below using examples that illustrate but do not limit the invention.
Исходные реагенты и физико-химические методы доказательства строения синтезированных веществ и их чистоты  Initial reagents and physicochemical methods for proving the structure of synthesized substances and their purity
Все растворители и реагенты были получены из коммерческих источников, таких как Sigmа-Аldriсh (США), Flukа (Германия), Асrоs (Бельгия) и Lапсаstеr (Англия). Точки плавления (т.пл.) были получены на приборе фирмы Вuсhi модель B-520. 1H и 13C ЯМР спектры были получены на спектрометрах фирмы Vаriап (300 МГц) в CDCl3, D2O и All solvents and reagents were obtained from commercial sources, such as Sigma-Aldrich (USA), Fluka (Germany), Acros (Belgium) and Lapsaster (England). Melting points (mp.) Were obtained on a Buxi model B-520 instrument. 1 H and 13 C NMR spectra were obtained on Variap (300 MHz) spectrometers in CDCl 3 , D 2 O and
64 64
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) DМSО-dб, химические сдвиги приведены в шкале δ (м.д.). Внутренний стандарт тетраметилсилан . SUBSTITUTE SHEET (RULE 26) DMSO-db, chemical shifts are given on a scale of δ (ppm). Internal standard tetramethylsilane.
Содержание основного вещества контролировали с помощью LC-MS на приборе Аррliеd Вiоsуstеms (Shimаdzu 10- AV LC, Gilson-215 автоматическая подача образца, масс- спектрометр API 150EX, детекторы UV (215 и 254 нм) и ELS, колонка Luna-C18, Рhепоmепех, 5 см х 2 мм). В соответствии с данными LС/МS все синтезированные соединения в спектрах MS имели молекулярный пик М+l, при этом содержание основного вещества во всех случаях было выше 95%.  The content of the main substance was monitored using LC-MS on an Arrlied BIOSystems instrument (Shimadzu 10-AV LC, Gilson-215 automatic sample feeding, API 150EX mass spectrometer, UV (215 and 254 nm) and ELS detectors, Luna-C18 column, Phepomepeh 5 cm x 2 mm). According to the data of LC / MS, all synthesized compounds in the MS spectra had a molecular peak M + l, while the content of the basic substance in all cases was higher than 95%.
Синтез замещенных индолов  Synthesis of substituted indoles
Смесь 50 ммоль замещенного фенилгидразина гидрохлорида и 6,95 г (50 ммоль) тропинона или другого 2 и (или) 6 замещенного пиперидона в 150 мл изопропанола кипятят 4 ч, затем охлаждают и пропускают HCl (газ), при этом смесь нагревается до кипения. Смесь кипятят еще 15 минут, растворитель упаривают, смесь обрабатывают водным поташом и экстрагируют МТБЭ (3* 100 мл). Экстракт сушат над поташом, упаривают и очищают методом колоночной хроматографии (CH2Cl2, MeOH, NH3 75:20:5). Получают индол в виде окрашенного твердого вещества. A mixture of 50 mmol of substituted phenylhydrazine hydrochloride and 6.95 g (50 mmol) of tropinone or another 2 and / or 6 substituted piperidone in 150 ml of isopropanol is boiled for 4 hours, then cooled and HCl (gas) is passed, while the mixture is heated to boiling. The mixture is boiled for another 15 minutes, the solvent is evaporated, the mixture is treated with aqueous potash and extracted with MTBE (3 * 100 ml). The extract was dried over potash, evaporated and purified by column chromatography (CH 2 Cl 2 , MeOH, NH 3 75: 20: 5). Indole is obtained as a colored solid.
2-Meтoкcи-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[ό]индoл  2-Methoxy-ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
Выход 36%. 1H NMR (400 МГц, CDCl3): 1.50-1.56 (м, IH), 1.85-1.95 (м, IH), 2.22-2.31 (м, 3H), 2.37 (с, 3H), 3.19 (дд, J = 4.3, 11.9 Гц, IH), 3.52-3.59 (м, IH), 3.85 (с, 3H), 4.17 (д, J = 4.8 Гц, IH), 6.75 (дд, J = 2.3, 6.3 Гц, IH), 6.90-6.95 (м, IH), 7.16 (д, J = 8.6 Гц, IH), 7.9 (уш. с, IH). Yield 36%. 1 H NMR (400 MHz, CDCl 3 ): 1.50-1.56 (m, IH), 1.85-1.95 (m, IH), 2.22-2.31 (m, 3H), 2.37 (s, 3H), 3.19 (dd, J = 4.3, 11.9 Hz, IH), 3.52-3.59 (m, IH), 3.85 (s, 3H), 4.17 (d, J = 4.8 Hz, IH), 6.75 (dd, J = 2.3, 6.3 Hz, IH) 6.90-6.95 (m, IH), 7.16 (d, J = 8.6 Hz, IH), 7.9 (br.s, IH).
2-Фтop-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[6]индoл  2-Ftop-ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole
Выход 41%. 1H NMR (400 МГц, CDCl3): 1.52-1.58 (м, IH), 1.81-1.95 (м, IH), 2.18-2.30 (м, 3H), 2.38 (с, 3H), 3.17-3,25 (м, IH), 3.50-3.59 (м, IH), 4.17 (д, J = 4.8 Гц, IH), 6.75 (дд, J = 2.2, 6.2 Гц, IH), 6.89-6.94 (м, IH), 7.17 (д, J = 8.4 Гц, IH), 7.8 (уш. с, IH). Yield 41%. 1 H NMR (400 MHz, CDCl 3 ): 1.52-1.58 (m, IH), 1.81-1.95 (m, IH), 2.18-2.30 (m, 3H), 2.38 (s, 3H), 3.17-3.25 (m, IH), 3.50-3.59 (m, IH), 4.17 (d, J = 4.8 Hz, IH), 6.75 (dd, J = 2.2, 6.2 Hz, IH), 6.89-6.94 (m, IH), 7.17 (d, J = 8.4 Hz, IH), 7.8 (br.s, IH).
ll-Meтил-6,7,8,9,10,ll-гeкcaгидpo-5H-7,10-эпиминoциклooктa[6]индoл ll-Methyl-6,7,8,9,10, ll-hexahydro-5H-7,10-epiminocyclooct [6] indole
Выход 51%, Тпл. 148-150 °C, ЯМР 1H (D6-ДMCO, 400 МГц): 1.00-1.14 (м, IH, CH2), 1.21- 1.29 (м, IH, CH2), 1.48-1.58 (м, 2H, CH2), 1.80-1.90 (м, 2H, CH2), 2.21 (с, ЗН, CH3), 2.35 (уш. д, 2J= 16.9 Гц, IH, CH2), 3.07-3.15 (м, 2H, CH2), 3.98 (уш.с, IH, CH), 6.85-6.70 (м, 2H, CH), 7.23-7.33 (м, 2H, CH), 10.74 (с, IH, NH). Yield 51%, mp. 148-150 ° C, 1 H NMR (D6-DMSO, 400 MHz): 1.00-1.14 (m, IH, CH 2 ), 1.21-1.29 (m, IH, CH 2 ), 1.48-1.58 (m, 2H, CH 2 ), 1.80-1.90 (m, 2H, CH 2 ), 2.21 (s, 3H, CH 3 ), 2.35 (brd, 2 J = 16.9 Hz, IH, CH 2 ), 3.07-3.15 (m, 2H, CH 2 ), 3.98 (br s, IH, CH), 6.85-6.70 (m, 2H, CH), 7.23-7.33 (m, 2H, CH), 10.74 (s, IH, NH).
2Дl-Димeтил-6,7,8,9Д0Дl-гeкcaгидpo-5//-7,10-эпиминoциклooктa[6]индoл  2Dl-Dimethyl-6,7,8,9D0Dl-hexahydro-5 // - 7,10-epiminocyclooct [6] indole
Выход 67%, Тпл. 158-159 0C, ЯМР 1H (D6-ДMCO, 400 МГц): 1.23-1.45 (м, 2H, CH2), 1.66 (уш.д, 2J= 13.4 Гц, IH, CH2), 1.76 (уш.д, 2J= 13.4 Гц, IH, CH2), 2.01-2.14 (м, 2H, CH2), 2.41 (с, ЗН, CH3), 2.43 (д, 2J= 17.1 Гц, IH, CH2), 2.49 (с, ЗН, CH3), 3.23 (дд, 2J= 17.1, 3J= 7.1 Гц, Yield 67%, mp. 158-159 0 C, 1 H NMR (D6-DMCO, 400 MHz): 1.23-1.45 (m, 2H, CH 2 ), 1.66 (br.s, 2 J = 13.4 Hz, IH, CH 2 ), 1.76 ( br.d., 2 J = 13.4 Hz, IH, CH 2 ), 2.01-2.14 (m, 2H, CH 2 ), 2.41 (s, 3Н, CH 3 ), 2.43 (d, 2 J = 17.1 Hz, IH, CH 2 ), 2.49 (s, 3H, CH 3 ), 3.23 (dd, 2 J = 17.1, 3 J = 7.1 Hz,
65 65
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) IH, CH2), 3.30-3.37 (м, IH, CHN), 4.19 (уш.с, IH, CHN), 7.00 (д, 3J= 8.0 Гц, IH, CH), 7.23-SUBSTITUTE SHEET (RULE 26) IH, CH 2 ), 3.30-3.37 (m, IH, CHN), 4.19 (br.s, IH, CHN), 7.00 (d, 3 J = 8.0 Hz, IH, CH), 7.23-
7.28 (м, 2H, CH), 8.40 (с, IH, NH). 7.28 (m, 2H, CH); 8.40 (s, IH, NH).
8-Фтop-2,3-Димeтил-2,3»4,5-τeтpaгидpo-lH-пиpидo[4,3-6]индoл 8-Ftop-2,3-Dimethyl-2,3 ” 4,5-tetrahydro-lH-pyrido [4,3-6] indole
Выход 28%. ЯМР 1H (D6-ДMCO, 400 МГц): J.07 (д, ЗН, J = 7 Гц), 2.35 (с, ЗН, CH3), 2.49Yield 28%. 1 H NMR (D6-DMSO, 400 MHz): J.07 (d, 3H, J = 7 Hz), 2.35 (s, 3H, CH 3 ), 2.49
(м, IH), 2.69 (м, IH), 3.40 (д, IH, J = 14 Гц), 3.70 (д, IH, J = 14 Гц), 6.82 (д, IH, J = 8 Гц),(m, IH), 2.69 (m, IH), 3.40 (d, IH, J = 14 Hz), 3.70 (d, IH, J = 14 Hz), 6.82 (d, IH, J = 8 Hz),
7.10 (м, 2H), 10.55 (уш. с, IH). 7.10 (m, 2H), 10.55 (br s, IH).
8-Meтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-6]индoл  8-Methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4.3-6] indole
Выход 19%. ЯМР 1H (D6-ДMCO, 400 МГц): 1.14 (д, ЗН, J = 7 Гц), 2.37 (с, ЗН, CH3), 2.42Yield 19%. 1 H NMR (D6-DMSO, 400 MHz): 1.14 (d, 3H, J = 7 Hz), 2.37 (s, 3H, CH 3 ), 2.42
(м, IH), 2.80 (м, IH), 3.50 (д, IH, J = 14.0 Гц), 3.70 (д, IH, J = 14.0 Гц), 3.75 (с, ЗН, CH3),(m, IH), 2.80 (m, IH), 3.50 (d, IH, J = 14.0 Hz), 3.70 (d, IH, J = 14.0 Hz), 3.75 (s, 3H, CH 3 ),
6.61 (д, IH, J = 8 Гц), 6.83 (с, IH), 7.21 (д, IH, J= 8 Гц), 10.8 (уш. с, IH). 6.61 (d, IH, J = 8 Hz), 6.83 (s, IH), 7.21 (d, IH, J = 8 Hz), 10.8 (br.s, IH).
2,3,8-Tpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-£]индoл  2,3,8-Trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4.3- £] indole
ЯМР 1H (D6-ДMCO, 400 МГц): 1.14 (д, ЗН, J = 7 Гц), 2.36 (с, ЗН, CH3), 2.40 (с, ЗН, CH3), 1 H NMR (D6-DMSO , 400 MHz): 1.14 (d, 3H, J = 7 Hz), 2.36 (s, 3H, CH 3 ), 2.40 (s, 3H, CH 3 ),
2.51 (м, IH), 2.83 (м, IH), 3.49 (д, IH, J= 14.0 Гц), 3.77 (д, IH, J= 14.0 Гц), 6.75 (д, IH, J =2.51 (m, IH), 2.83 (m, IH), 3.49 (d, IH, J = 14.0 Hz), 3.77 (d, IH, J = 14.0 Hz), 6.75 (d, IH, J =
8 Гц), 7.07 (с, IH), 7.15 (д, IH, J= 8 Гц), 10.55 (уш. с, IH). 8 Hz), 7.07 (s, IH), 7.15 (d, IH, J = 8 Hz), 10.55 (br.s, IH).
2,3-Димeтил-2,3,4,5-тeтpaгидpo-li/-пиpидo[4,3-Λ]индoл 2,3-Dimethyl-2,3,4,5-tetrahydro-li / pyrido [4,3-Λ] indole
Выход 30%. ЯМР 1H (D6-ДMCO, 400 МГц): 1.12 (д, ЗН, J = 7 Гц), 2.41 (с, ЗН, CH3), 2.49 (м, IH), 2.81 (м, IH), 3.51 (д, IH, J = 14.5 Гц), 3.75 (д, IH, J = 14.5 Гц), 6.93 (т, IH, J = 8Yield 30%. 1 H NMR (D6-DMSO , 400 MHz): 1.12 (d, 3H, J = 7 Hz), 2.41 (s, 3H, CH 3 ), 2.49 (m, IH), 2.81 (m, IH), 3.51 ( d, IH, J = 14.5 Hz), 3.75 (d, IH, J = 14.5 Hz), 6.93 (t, IH, J = 8
Гц), 7.01 (т, IH, J= 8 Гц), 7.26 (д, IH, J= 8 Гц), 7.32 (д, IH, J= 8 Гц),- 10.7 (уш. с, IH). Hz), 7.01 (t, IH, J = 8 Hz), 7.26 (d, IH, J = 8 Hz), 7.32 (d, IH, J = 8 Hz), - 10.7 (br.s, IH).
8-Xлop-2,3-Димeтил-2,354,5-тeтpaгидpo-l//-пиpидo[4,3-^]индoл 8-Chloro-2,3- D methyl-2,3 5 4,5-tetrahydro-l // - pyrido [4,3 - ^] indole
Выход 57%. ЯМР 1H (D6-ДMCO, 400 МГц): 1.07 (д, ЗН, J = 7 Гц), 2.35 (с, ЗН, CH3), 2.49 (м, IH), 2.79 (м, IH), 3.47 (д, IH, J = 14 Гц), 3.69 (д, IH, J = 14 Гц), 6.97 (д, IH, J = 8 Гц), 7.31 (д, IH5 J= 8 Гц), 7.35 (с, IH), 10.8 (уш. с, IH). Yield 57%. 1 H NMR (D6-DMSO , 400 MHz): 1.07 (d, 3H, J = 7 Hz), 2.35 (s, 3H, CH 3 ), 2.49 (m, IH), 2.79 (m, IH), 3.47 ( d, IH, J = 14 Hz), 3.69 (d, IH, J = 14 Hz), 6.97 (d, IH, J = 8 Hz), 7.31 (d, IH 5 J = 8 Hz), 7.35 (s, IH), 10.8 (br.s, IH).
8,8-Димeтил-3-oкco-8-aзoниa-бицикл о [3.2.1 ] октан иодид 8,8-Dimethyl-3-oxo-8-azonia-bicyclo o [3.2.1] octane iodide
Тропинон (5.2 г, 37.4 ммоль, 1 экв) растворяют в 37 мл ацетона при перемешивании. Йодистый метил (2.5 мл, 41.2 ммоль, 1.1 экв) добавляют по каплям при перемешивании в течение 45 мин. Реакционную смесь перемешивают при комнатной температуре еще 1 час. Осадок отфильтровывают и промывают ацетоном и гексаном. Сушат в вакууме. Выход 5.61 г (92%), белые кристаллы. Tropinone (5.2 g, 37.4 mmol, 1 equiv) is dissolved in 37 ml of acetone with stirring. Methyl iodide (2.5 ml, 41.2 mmol, 1.1 eq) was added dropwise with stirring over 45 minutes. The reaction mixture was stirred at room temperature for another 1 hour. The precipitate was filtered off and washed with acetone and hexane. Dried in a vacuum. Yield 5.61 g (92%), white crystals.
ЯМР 1H (ДМСО, 300 МГц): 4.17 (м, 2H), 3.39 (с, ЗН), 3.19 (с, ЗН), 2.50 (м, 2H), 1.95 (м, IH). 1 H NMR (DMSO, 300 MHz): 4.17 (m, 2H), 3.39 (s, 3H), 3.19 (s, 3H), 2.50 (m, 2H), 1.95 (m, IH).
Общая методика синтеза замещенных тропинонов  General method for the synthesis of substituted tropinones
Циклогексиламин (1.6 мл, 14 ммоль, 1 экв) или другой амин растворяют в 32 мл этанола, добавляют раствор K2CO3 (4.05 г, 29 ммоль, 2.1 экв) в 11 мл дистиллированной воды. Полученный раствор доводят до кипения. Раствор IDABO (4.48 г, 16 ммоль, 1.1 экв) в 25 мл дистиллированной воды добавляют по каплям в течение 45 мин. Реакционную смесь Cyclohexylamine (1.6 ml, 14 mmol, 1 equiv) or another amine is dissolved in 32 ml of ethanol, a solution of K 2 CO 3 (4.05 g, 29 mmol, 2.1 equiv) in 11 ml of distilled water is added. The resulting solution was brought to a boil. A solution of IDABO (4.48 g, 16 mmol, 1.1 eq) in 25 ml of distilled water was added dropwise over 45 minutes. Reaction mixture
66 66
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) кипятят еще 4 часа, охлаждают, раствор концентрируют в вакууме.- Остаток экстрагирую хлористым метиленом (Зχ25 мл), промывают насыщенным раствором NaCl (2x15 мл), сушат Na2SO4 и концентрируют в вакууме. Продукт выделяют методом колоночной хроматографии (SiO2, гексан/этилацетат 1 :1). Полученный продукт растворяют в 10 мл эфира и добавляют по каплям 10 мл IN HCl в эфире. Раствор концентрируют, остаток сушат в вакууме. SUBSTITUTE SHEET (RULE 26) boil for another 4 hours, cool, the solution is concentrated in vacuo. - The residue is extracted with methylene chloride (3 x 25 ml), washed with saturated NaCl solution (2x15 ml), dried with Na 2 SO 4 and concentrated in vacuo. The product was isolated by column chromatography (SiO 2 , hexane / ethyl acetate 1: 1). The resulting product was dissolved in 10 ml of ether and 10 ml of IN HCl in ether was added dropwise. The solution was concentrated, the residue was dried in vacuo.
8-Циклoгeкcил-8-aзaбициклo[3.2.1]oктaн-3-oн гидрохлорид, выход 52%, Тпл. 224.5- 225.0 0C 8-Cyclohexyl-8-azabicyclo [3.2.1] octan-3-one hydrochloride, yield 52%, mp. 224.5- 225.0 0 C
8-Бeнзил-8-aзaбициклo[3.2.1]oктaн-3-oн гидрохлорид, выход 50%, Тпл. 195.0-196.00C Синтез 11- замещенных 5,6,7,8,9,10-гeкcaгидpo-7,10гэпиминoциклoгeптa[6]индoлoв Смесь амина гидрохлорида (61.9 ммоль, 1 экв.) и арилгидразина (71.2 ммоль, 1.15 экв) кипятят в 175 мл абсолютного нзо-пропанола в течение 30 мин. Реакционную смесь охлаждают до комнатной температуры, насыщают газообразным HCl и кипятят в течение 2-6 часов. Реакционную смесь концентрируют в вакууме, полученный коричневый остаток растворяют в 50 мл воды. К полученному раствору по каплям добавляют насыщенный раствор аммиака до рН 9-10. Раствор экстрагируют хлористым метиленом (Зχ25 ml), сушат Na2SO4 и концентрируют в вакууме. Продукт выделяют методом колоночной хроматографии (SiO2, CH2Cl2 - CH2Cl2/Me0H 3:1). 8-Benzyl-8-azabicyclo [3.2.1] octan-3-one hydrochloride, yield 50%, mp. 195.0-196.0 0 C Synthesis of 11-substituted 5,6,7,8,9,10-hexahydro-7.10 g epiminocyclohept [6] indoles A mixture of amine hydrochloride (61.9 mmol, 1 equiv.) And aryl hydrazine (71.2 mmol, 1.15 eq.) is boiled in 175 ml of absolute nzo-propanol for 30 minutes. The reaction mixture was cooled to room temperature, saturated with gaseous HCl and boiled for 2-6 hours. The reaction mixture was concentrated in vacuo, the resulting brown residue was dissolved in 50 ml of water. Saturated ammonia solution was added dropwise to the resulting solution to a pH of 9-10. The solution was extracted with methylene chloride (3 x 25 ml), dried with Na 2 SO 4 and concentrated in vacuo. The product was isolated by column chromatography (SiO 2 , CH 2 Cl 2 - CH 2 Cl 2 / Me0H 3: 1).
ll-Циклoгeкcил-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[6]индoл, выход 23%, Тпл 200-202 0C, ЯМР 1H (CDCl3, δ, м.д.): 0.72-0.90 (м, IH), 0.96-1.10 (м, 3H), 1.40-1.50 (м, IH), 1.55-1.64 (м, IH), 1.66-1.85 (м, 4H), 1.89-2.01 (м, 2H), 2.04 (т, 3J = 10.9 Гц, IH), 2.45- 2.58 (м, IH), 2.64-2.75 (м, IH), 2.75-2.85 (м, IH), 2.90 (д, 2J= 17.7 Гц, IH), 4.26 (уш.с, IH), 5.02 (д, 3J= 4.8 Гц, IH), 6.97-7.10 (м, 2H), 7.31 (д, 3J= 7.3 Гц, IH), 7.41 (д, 3J= 7.8 Гц, IH), 10.90 (с, IH). ll-Cyclohexyl-5,6,7,8,9,10-hexahydro-7,10-epiminocycloheptol [6] indole, 23% yield, mp 200-202 0 C, 1 H NMR (CDCl 3, δ, m. d): 0.72-0.90 (m, IH), 0.96-1.10 (m, 3H), 1.40-1.50 (m, IH), 1.55-1.64 (m, IH), 1.66-1.85 (m, 4H), 1.89 -2.01 (m, 2H), 2.04 (t, 3 J = 10.9 Hz, IH), 2.45-2.58 (m, IH), 2.64-2.75 (m, IH), 2.75-2.85 (m, IH), 2.90 ( d, 2 J = 17.7 Hz, IH), 4.26 (br.s, IH), 5.02 (d, 3 J = 4.8 Hz, IH), 6.97-7.10 (m, 2H), 7.31 (d, 3 J = 7.3 Hz, IH), 7.41 (d, 3 J = 7.8 Hz, IH), 10.90 (s, IH).
ll-Бeнзил-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[Z»]индoл, выход 20%, Тпл 184-185 0C, ЯМР 1H (CDCl3, δ, м.д.): 1.55-1.66 (м, IH), 1.92-2.03 (м, IH), 2.32-2.45 (м, 2H), 2.49 (д, 2J- 16.8 Гц, IH), 3.33 (дц, 2J= 16.8, 3J= 4.1 Гц, IH), 3.76 (д, 2J= 12.9 Гц, IH), 3.82- 3.86 (м, IH), 3.83 (д, 2J = 12.9 Гц, IH), 4.37 (д, 2J = 4.1 Гц, IH), 7.07-7.17 (м, 2H), 7.27-7.32 (м, 3H), 7.33-7.40 (м, 4H), 9.26 (с, IH). ll-Benzyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [Z ”] indole, 20% yield, mp 184-185 0 C, 1 H NMR (CDCl 3, δ, m etc.): 1.55-1.66 (m, IH), 1.92-2.03 (m, IH), 2.32-2.45 (m, 2H), 2.49 (d, 2 J-16.8 Hz, IH), 3.33 (dts, 2 J = 16.8, 3 J = 4.1 Hz, IH), 3.76 (d, 2 J = 12.9 Hz, IH), 3.82- 3.86 (m, IH), 3.83 (d, 2 J = 12.9 Hz, IH), 4.37 ( d, 2 J = 4.1 Hz, IH), 7.07-7.17 (m, 2H), 7.27-7.32 (m, 3H), 7.33-7.40 (m, 4H), 9.26 (s, IH).
Общая методика получения lH-индoл-2-илмeтaнoлoв General procedure for the preparation of lH-indol-2-ylmethanols
К суспензии 2.1 экв, 0.65 моль литийалюмогидрида в смеси абсолютных ТГФ и эфира (250 + 250 мл) при интенсивном перемешивании порциями аккуратно присыпали 0.31 моль 2- индолилкарбоновой кислоты с такой скоростью, чтобы растворители кипели не слишком бурно. По окончании прибавления смесь кипятили 1.5 ч и оставляли на ночь. Полученную реакуионную смесь разлагали аккуратным прибавлением 75 мл 10% водного раствора To a suspension of 2.1 eq, 0.65 mol of lithium aluminum hydride in a mixture of absolute THF and ether (250 + 250 ml), with vigorous stirring, 0.31 mol of 2-indolylcarboxylic acid was carefully poured in portions at such a rate that the solvents did not boil too violently. Upon completion of the addition, the mixture was boiled for 1.5 h and left overnight. The resulting reaction mixture was decomposed by the careful addition of 75 ml of a 10% aqueous solution.
67  67
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) гидроксида натрия, фильтровали, остаток на фильтре промывали горячим ТГФ (2*250 мл), объединенный экстракт упаривали, растворяли в минимальном объеме хлористого метилена, сушили над поташом и снова упаривали. SUBSTITUTE SHEET (RULE 26) sodium hydroxide, filtered, the filter residue was washed with hot THF (2 * 250 ml), the combined extract was evaporated, dissolved in a minimum volume of methylene chloride, dried over potash and evaporated again.
lЯ-индoл-2-илмeтaнoл, выход 98%, Тпл. 74-75 С. Спектр 1H ЯМР (400 МГц, CDCl3): 12.41 ( уш. с, IH, ОН), 4.74 (с, 2H, CH2-Ar), 6.39 (с, IH, Ar-H), 7.12-7.21 (м, 2H, Ar-H), 7.27- 7.30 (м, IH, Ar-H), 7.60 (д, J= 7.1 Гц, IH, Ar-H), 8.39 (уш. с, IH, NH). l-Indol-2-ylmethanol, yield 98%, mp. 74-75 C. Spectrum 1 H NMR (400 MHz, CDCl 3 ): 12.41 (br s, IH, OH), 4.74 (s, 2H, CH 2 -Ar), 6.39 (s, IH, Ar-H) , 7.12-7.21 (m, 2H, Ar-H), 7.27-7.30 (m, IH, Ar-H), 7.60 (d, J = 7.1 Hz, IH, Ar-H), 8.39 (br.s, IH , NH).
5-Meтил-l#-индoл-2-илмeтaнoл, выход 97%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.92 (уш. с, IH, ОН), 2.45 (с, ЗН, CH3-Ar), 4.79 (с, 2H, CH2-Ar), 6.33 (с, IH, Ar-H), 7.02 (д, IH, J = 8.2 Гц, Ar-H), 7.23 (д, IH, J = 8.2 Гц, Ar-H), 7.38 (с, IH, Ar-H), 8.25 (уш. с, IH, NH). 5-Methyl-l #-indol-2-ylmethanol, yield 97%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.92 (br s, IH, OH), 2.45 (s, 3H, CH 3 -Ar), 4.79 (s, 2H, CH 2 -Ar), 6.33 (s , IH, Ar-H), 7.02 (d, IH, J = 8.2 Hz, Ar-H), 7.23 (d, IH, J = 8.2 Hz, Ar-H), 7.38 (s, IH, Ar-H) 8.25 (br.s, IH, NH).
5-Meтoкcи-lЯ-индoл-2-илмeтaнoл, выход 98%. Спектр 1H ЯМР (400 МГц, CDCl3): 3.71 (с, ЗН, CH3O), 4.56 (с, 2H, J= 6.1 Гц, CH2-Ar), 5.20 (t, IH, J= 6.1 Гц, ОН), 6.18 (с, IH, Ar- H), 6.67 (д, IH, J = 8.5 Гц, Ar-H), 6.95 (с, IH, Ar-H), 7.19 (д, J = 8.5 Гц, IH, Ar-H), 10.81 (уш. с, IH, NH). 5-Methoxy-l-indol-2-ylmethanol, yield 98%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 3.71 (s, 3H, CH 3 O), 4.56 (s, 2H, J = 6.1 Hz, CH 2 -Ar), 5.20 (t, IH, J = 6.1 Hz , OH), 6.18 (s, IH, Ar-H), 6.67 (d, IH, J = 8.5 Hz, Ar-H), 6.95 (s, IH, Ar-H), 7.19 (d, J = 8.5 Hz , IH, Ar-H), 10.81 (br s, IH, NH).
5-Фтop-lЯ-индoл-2-илмeтaнoл, выход 99%. Спектр 1H ЯМР (400 МГц, CDCl3): 5.21 (с, 2H, CH2-Ar), 6.77 (с, IH, Ar-H), 7.30 (т, J= 9.2 Гц, IH, Ar-H), 7.63 (дд, J = 10.1 и 2.5 Гц, IH, Ar-H), 7.81 (дд, J= 9.2 и 4.5 Гц, IH, Ar-H), 10.71 (уш. с, IH, NH) 5-Ftop-lJ-indol-2-ylmethanol, 99% yield. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 5.21 (s, 2H, CH 2 -Ar), 6.77 (s, IH, Ar-H), 7.30 (t, J = 9.2 Hz, IH, Ar-H) , 7.63 (dd, J = 10.1 and 2.5 Hz, IH, Ar-H), 7.81 (dd, J = 9.2 and 4.5 Hz, IH, Ar-H), 10.71 (br.s, IH, NH)
5-Xлop-l#-индoл-2-илмeтaнoл, выход 96%. Спектр 1H ЯМР (400 МГц, CDCl3): 4.60 (с, 2H, CH2-Ar), 6.25 (с, IH, Ar-H), 7.01 (д, J= 8.5 Гц, IH, Ar-H), 7.30 (д, J= 8.5 Гц, IH, Ar-H), 7.48 (уш. с, IH, Ar-H), 11.20 (уш. с, IH, NH). 5-Chlor-l #-indol-2-ylmethanol, 96% yield. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 4.60 (s, 2H, CH 2 -Ar), 6.25 (s, IH, Ar-H), 7.01 (d, J = 8.5 Hz, IH, Ar-H) 7.30 (d, J = 8.5 Hz, IH, Ar-H), 7.48 (br.s, IH, Ar-H), 11.20 (br.s, IH, NH).
Общая методика получения lЯ-индoл-2-илмeтилбeнзoaтoвGeneral procedure for the preparation of lЯ-indol-2-ylmethylbenzene
К раствору 0.307 моль полученного выше спирта в 400 мл хлористого метилена приливали 60 мл 2.5 экв, 0.8 моль сухого пиридина, охлаждали до 0 0C и при перемешивании прибавляли по каплям 38 мл (46 г, 1.07 экв, 0.33 моль) бензоилхлорида, следя за тем, чтобы температура не превышала 10 0C. По окончаний прибавление реакционную смесь перемешивали дополнительные 12 ч, затем тщательно упаривали, обрабатывали ледяным IN раствором соляной кислоты, кристаллы отфильтровывали, промывали водой, затем холодным эфиром (200 мл), тщательно отжимали и сушили в вакууме 12 ч. To a solution of 0.307 mol of the alcohol obtained above in 400 ml of methylene chloride was added 60 ml of 2.5 equiv, 0.8 mol of dry pyridine, cooled to 0 0 C, and 38 ml (46 g, 1.07 equiv, 0.33 mol) of benzoyl chloride were added dropwise with monitoring so that the temperature does not exceed 10 0 C. At the end of the addition, the reaction mixture was stirred for an additional 12 hours, then thoroughly evaporated, treated with ice-cold IN hydrochloric acid solution, the crystals were filtered off, washed with water, then with cold ether (200 ml), carefully wrung out and dried in vacuum 12 hours
lЯ-Индoл-2-илмeтилбeнзoaтa, выход 79%. Тпл. 123-124 С. Спектр 1H ЯМР (400 МГц, ДMCO-d6): 5.48 (с, 2H, CH2-Ar), 6.56 (с, IH, Ar-H), 6.98-7.13 (м, 2H, Ar-H), 7.39-7.41 (м, IH, Ar-H), 7.50-7.55 (м, ЗН, Ar-H), 7.62-7.64 (м, IH, Ar-H), 8.01-8.03 (м, 2H, Ar-H), 11.36 (уш. с, IH, NH). l-Indol-2-ylmethylbenzoate, yield 79%. Mp 123-124 C. Spectrum 1 H NMR (400 MHz, DMSO-d 6 ): 5.48 (s, 2H, CH 2 -Ar), 6.56 (s, IH, Ar-H), 6.98-7.13 (m, 2H, Ar-H), 7.39-7.41 (m, IH, Ar-H), 7.50-7.55 (m, 3Н, Ar-H), 7.62-7.64 (m, IH, Ar-H), 8.01-8.03 (m, 2H, Ar-H), 11.36 (br s, IH, NH).
(5-Meтил-lЯ-индoл-2-ил)мeтил бензоат Спектр 1H ЯМР (400 МГц, ДMCO-d6): 2.35 (с, ЗН, CH3-Ar), 5.44 (с, 2H, CH2-Ar), 6.44 (с, IH, Ar-H), 6.92 (д, IH, J= 8.1 Гц, Ar-H), 7.27 (д, (5-Methyl-lH-indol-2-yl) methyl benzoate Spectrum 1 H NMR (400 MHz, DMSO-d 6 ): 2.35 (s, 3H, CH 3 -Ar), 5.44 (s, 2H, CH 2 - Ar), 6.44 (s, IH, Ar-H), 6.92 (d, IH, J = 8.1 Hz, Ar-H), 7.27 (d,
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) IH, J = 8.1 Гц, Ar-H), 7.29 (с, IH, Ar-H), 7.50-7.65 (м, ЗН, Ar-H), 7.98-8.02 (м, 2H, Ar-H),SUBSTITUTE SHEET (RULE 26) IH, J = 8.1 Hz, Ar-H), 7.29 (s, IH, Ar-H), 7.50-7.65 (m, 3Н, Ar-H), 7.98-8.02 (m, 2H, Ar-H),
11.18 (уш. с, IH, NH). 11.18 (br.s, IH, NH).
(5-Meтoкcи-lЯ-индoл-2-ил)мeтил бензоат Спектр 1H ЯМР (400 МГц, JЩCO-d6): 3.73 (с, ЗН, CH3O), 5.43 (с, 2H, CH2-Ar), 6.46 (с, IH, Ar-H), 6.73 (д, IH, J - 8.3 Гц, Ar-H), 7.01 (с, IH, Ar-H), 7.26 (д, J = 8.3 Гц, IH, Ar-H), 7.50-7.55 (м, ЗН, Ar-H), 7.99-8.01 (м, 2H, Ar-H), 11.16 (уш. с, IH, NH). (5-Methoxy-l-indol-2-yl) methyl benzoate Spectrum 1 H NMR (400 MHz, JSCCO-d 6 ): 3.73 (s, 3H, CH 3 O), 5.43 (s, 2H, CH 2 -Ar ), 6.46 (s, IH, Ar-H), 6.73 (d, IH, J - 8.3 Hz, Ar-H), 7.01 (s, IH, Ar-H), 7.26 (d, J = 8.3 Hz, IH , Ar-H), 7.50-7.55 (m, 3Н, Ar-H), 7.99-8.01 (m, 2H, Ar-H), 11.16 (br.s, IH, NH).
(5-Xлop-lЯ-Индoл-2-ил)мeтил бензоат, выход 90%. Спектр 1H ЯМР (400 МГц, DMSO- d6): 5.47 (с, 2H, CH2-Ar), 6.54 (с, IH, Ar-H), 7.10 (д, J= 8.6 Гц, IH, Ar-H), 7.40 (д, J= 8.6 Гц, IH, Ar-H), 7.52-7.67 (м, 4H, Ar-H), 8.00-8.02 (м, 2H, Ar-H), 11.55 (уш.'с, IH, NH). (5-Chlorop-l-Indol-2-yl) methyl benzoate, yield 90%. 1 H NMR spectrum (400 MHz, DMSO-d 6 ): 5.47 (s, 2H, CH 2 -Ar), 6.54 (s, IH, Ar-H), 7.10 (d, J = 8.6 Hz, IH, Ar- H), 7.40 (d, J = 8.6 Hz, IH, Ar-H), 7.52-7.67 (m, 4H, Ar-H), 8.00-8.02 (m, 2H, Ar-H), 11.55 (br. ' s, IH, NH).
(5-Фтop-lЯ-Индoл-2-ил)мeтил бензоат, выход 90%. Спектр 1H ЯМР (400 МГц, DMSO- d6): 5.97 (с, 2H, CH2-Ar), 7.07 (с, IH, Ar-H), 7.38 (т, IH, J = 9.0 Гц, Ar-H), 7.72 (дд, IH, J = 9.9 и 2.3 Гц, Ar-H), 7.87 (дд, J = 9.0 и 4.6 Гц, IH, Ar-H), 7.94-8.10 (м, ЗН, Ar-H), 8.47-8.50 (м, 2H, Ar-H), 10.97 (уш. с, IH, NH). (5-Ftop-l-Indo-2-yl) methyl benzoate, yield 90%. 1 H NMR spectrum (400 MHz, DMSO-d 6 ): 5.97 (s, 2H, CH 2 -Ar), 7.07 (s, IH, Ar-H), 7.38 (t, IH, J = 9.0 Hz, Ar- H), 7.72 (dd, IH, J = 9.9 and 2.3 Hz, Ar-H), 7.87 (dd, J = 9.0 and 4.6 Hz, IH, Ar-H), 7.94-8.10 (m, ЗН, Ar-H ), 8.47-8.50 (m, 2H, Ar-H), 10.97 (br s, IH, NH).
Общая методика получения lЯ-индoл-2-илaцeтoнитpилoвGeneral procedure for the preparation of l-indol-2-ylacetonitriles
К раствору 0.23 моль полученного выше бензоата в 400 мл сухого ДМФА присыпали 60 г (5 экв, 1.2 моль) цианида натрия, перемешивали 1 ч и медленно нагревали. При температуре выше 80 0C начинается экзотермичная реакция поэтому реакционную смесь необходимо охлаждать так, что бы температура не превышала 1Q0 °C. По окончании бурной реакции смесь интенсивно перемешивают дополнительные 45 мин при 80 0C и выливают в 1 л холодной воды. Полученные нитрил тщательно экстрагируют толуолом (4*300 мл), объединенный экстракт промывают рассолом, сушат над хлористым кальцием (примесь - спирт!), упаривают и дополнительно очищают методом колоночной хроматографии (элюент - хлористый метилен), нужные фракции упаривают и при необходимости дополнительно промывают небольшим объемом тетрахлорметана с несколькими каплями ацетона. To a solution of 0.23 mol of the benzoate obtained above in 400 ml of dry DMF was added 60 g (5 eq, 1.2 mol) of sodium cyanide, stirred for 1 h and slowly heated. At temperatures above 80 0 C, an exothermic reaction begins; therefore, the reaction mixture must be cooled so that the temperature does not exceed 1Q0 ° C. At the end of the violent reaction, the mixture is intensively stirred for an additional 45 minutes at 80 ° C and poured into 1 liter of cold water. The obtained nitrile is carefully extracted with toluene (4 * 300 ml), the combined extract is washed with brine, dried over calcium chloride (admixture is alcohol!), Evaporated and further purified by column chromatography (eluent is methylene chloride), the desired fractions are evaporated and, if necessary, additionally washed a small volume of carbon tetrachloride with a few drops of acetone.
lЯ-Индoл-2-илaцeтoнитpил, выход 61%. Тпл. 94-95 С. Спектр 1H ЯМР (400 МГц, CDCl3): 3.86 (с, 2H, CH2-Ar), 6.49 (с, IH, Ar-H), 7.15-7.27 (м, 2H, Ar-H), 7.34 (д, J= 6.9 Гц, IH, Ar-H), 7.61 (д, J= 7.1 Гц, IH, Ar-H), 8.34 (уш. с, IH, NH). l-Indol-2-ylacetonitrile, yield 61%. Mp 94-95 C. Spectrum 1 H NMR (400 MHz, CDCl 3 ): 3.86 (s, 2H, CH 2 -Ar), 6.49 (s, IH, Ar-H), 7.15-7.27 (m, 2H, Ar- H), 7.34 (d, J = 6.9 Hz, IH, Ar-H), 7.61 (d, J = 7.1 Hz, IH, Ar-H), 8.34 (br.s, IH, NH).
5-Meтил-lЯ-индoл-2-илaцeтoнитpил , выход 50%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.34 (с, ЗН, CH3-Ar), 4.79 (с, 2H, CH2-Ar), 4.16 (с, 2H, CH2-Ar), 6.35 (с, IH, Ar-H), 7.03 (д, IH, J= 8.2 Гц, Ar-H), 7.24 (д, IH, J= 8.2 Гц, Ar-H), 7.38 (с, IH, Ar-H), 8.35 (уш. с, IH, NH). 5-Meтoкcи-lЯ-индoл-2-илaцeтoнитpил, выход 44%. Спектр 1H ЯМР (400 МГц, ДМСО- d6): 3.73 (с, ЗН, CH3O), 4.14 (с, 2H, CH2-Ar), 6.29 (с, IH, Ar-H), 6.72 (д, IH, J = 8.5 Гц, Ar- H), 6.99 (с, IH, Ar-H), 7.23 (д, J= 8.5 Гц, IH, Ar-H), 11.20 (уш. с, IH, NH). 5-Methyl-lH-indol-2-ylacetonitrile, yield 50%. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 2.34 (s, 3H, CH 3 -Ar), 4.79 (s, 2H, CH 2 -Ar), 4.16 (s, 2H, CH 2 -Ar), 6.35 ( s, IH, Ar-H), 7.03 (d, IH, J = 8.2 Hz, Ar-H), 7.24 (d, IH, J = 8.2 Hz, Ar-H), 7.38 (s, IH, Ar-H ), 8.35 (br.s, IH, NH). 5-Methoxy-l-indol-2-yl-acetonitrile, 44% yield. 1 H NMR spectrum (400 MHz, DMSO-d 6 ): 3.73 (s, 3H, CH 3 O), 4.14 (s, 2H, CH 2 -Ar), 6.29 (s, IH, Ar-H), 6.72 ( d, IH, J = 8.5 Hz, Ar-H), 6.99 (s, IH, Ar-H), 7.23 (d, J = 8.5 Hz, IH, Ar-H), 11.20 (br.s, IH, NH )
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 5-Xлop-Ш-индoл-2-илaцeтoнитpил, выход 60%. Спектр 1H ЯМР (400 МГц, CDCl3): 4.21 (с, 2H, CH2-Ar), 6.39 (с, IH, Ar-H), 7.08 (д, J= 8.6 Гц, IH, Ar-H), 7.36 (д, J- 8.6 Гц, IH, Ar- H), 7.54 (уш. с, IH, Ar-H), 11.51 (уш. с, IH, NH). SUBSTITUTE SHEET (RULE 26) 5-Chlorop-III-indol-2-ylacetonitrile, yield 60%. Spectrum 1 H NMR (400 MHz, CDCl 3 ): 4.21 (s, 2H, CH 2 -Ar), 6.39 (s, IH, Ar-H), 7.08 (d, J = 8.6 Hz, IH, Ar-H) 7.36 (d, J-8.6 Hz, IH, Ar-H), 7.54 (br.s, IH, Ar-H), 11.51 (br.s, IH, NH).
5-Фтop-l#-индoл-2-илaцeтoнитpил, выход 60%. Спектр 1H ЯМР (400 МГц, CDCl3): 4.19 (с, 2H, CH2-Ar), 6.38 (с, IH, Ar-H), 6.92 (дд, J = 9.0 и 2.2 Гц, IH, Ar-H), 7.26 (дд, J = 9.9 и 2.2 Гц, IH, Ar-H), 7.35 (дд, J= 9.0 и 4.6 Гц, IH, Ar-H), 11.39 (уш. с, IH, NH). 5-FT-l #-indol-2-ylacetonitrile, 60% yield. 1 H NMR spectrum (400 MHz, CDCl 3 ): 4.19 (s, 2H, CH 2 -Ar), 6.38 (s, IH, Ar-H), 6.92 (dd, J = 9.0 and 2.2 Hz, IH, Ar- H), 7.26 (dd, J = 9.9 and 2.2 Hz, IH, Ar-H), 7.35 (dd, J = 9.0 and 4.6 Hz, IH, Ar-H), 11.39 (br.s, IH, NH).
Общая методика получения lH-индoл-2-илэтилaминoвGeneral procedure for the preparation of lH-indol-2-yl-ethyl amines
Полученный выше нитрил (0.07 моль) растворяют в 250 мл метанола, насыщенного аммиаком, прибавляют 1 г никеля Рэнея и гидрируют при давлении водорода 100 атм и комнатной температуре в течение 12 ч. Затем реакционную массу фильтруют через целити тщательно упаривают. The nitrile (0.07 mol) obtained above was dissolved in 250 ml of methanol saturated with ammonia, 1 g of Rayney nickel was added, and it was hydrogenated at a hydrogen pressure of 100 atm and room temperature for 12 hours. Then the reaction mixture was filtered through celite and carefully evaporated.
lЯ-Индoл-2-илэтилaмин, выход 98%. Тпл. 92-94 С. Спектр 1H ЯМР (400 МГц, ДМСО- d6): 2.73-2.80 (м, 2H5 CH2-Ar), 2.84-2.90 (м, 2H, CH2-N), 6.12 (с, IH, Ar-H), 6.88-6.99 (м, 2H,l-Indol-2-yl-ethylamine, yield 98%. Mp 92-94 C. Spectrum 1 H NMR (400 MHz, DMSO-d 6 ): 2.73-2.80 (m, 2H 5 CH 2 -Ar), 2.84-2.90 (m, 2H, CH 2 -N), 6.12 (s , IH, Ar-H), 6.88-6.99 (m, 2H,
Ar-H), 7.26 (д, J= 7.0 Гц, IH, Ar-H), 7.39 (д, J= 7.2 Гц, IH, Ar-H), 10.92 (уш. с, IH, NH).Ar-H), 7.26 (d, J = 7.0 Hz, IH, Ar-H), 7.39 (d, J = 7.2 Hz, IH, Ar-H), 10.92 (br.s, IH, NH).
5-Meтил-l#-Индoл-2-илэтилaмин, выход 90%. Спектр 1H ЯМР (400 МГц, JЩCO-d6):5-Methyl-l #-indol-2-yl-ethylamine, 90% yield. Spectrum 1 H NMR (400 MHz, JSCCO-d 6 ):
2.32 (с, ЗН, CH3-Ar), 2.71-2.75 (м, 2H, CH2-Ar), 2.83-2.88 (м, 2H, CH2-N), 6.03 (с, IH, Ar-H),2.32 (s, 3H, CH 3 -Ar), 2.71-2.75 (m, 2H, CH 2 -Ar), 2.83-2.88 (m, 2H, CH 2 -N), 6.03 (s, IH, Ar-H) ,
6.79 (д, IH, J= 8.1 Гц, Ar-H), 7.14 (д, IH, J = 8.1 Гц, Ar-H), 7.16 (с, IH, Ar-H), 10.75 (уш. с,6.79 (d, IH, J = 8.1 Hz, Ar-H), 7.14 (d, IH, J = 8.1 Hz, Ar-H), 7.16 (s, IH, Ar-H), 10.75 (br.
IH5 NH). IH 5 NH).
5-Meтoкcи-lЯ-Индoл-2-илэтилaмин, выход 60%. Спектр 1H ЯМР (400 МГц, JЩCO-d6):5-Methoxy-l-Indol-2-yl-ethylamine, yield 60%. Spectrum 1 H NMR (400 MHz, JSCCO-d 6 ):
2.72-2.76 (м, 2H, CH2-Ar), 2.84-2.89 (м, 2H, CH2-N), 3.71 (с, ЗН, CH3O), 6.05 (с, IH, Ar-H)5 2.72-2.76 (m, 2H, CH 2 -Ar), 2.84-2.89 (m, 2H, CH 2 -N), 3.71 (s, 3H, CH 3 O), 6.05 (s, IH, Ar-H) 5
6.62 (д, IH, J= 8.0 Гц, Ar-H), 6.91(c, IH, Ar-H), 7.14 (д, J= 8.0 Гц, IH5 Ar-H), 10.72 (уш. с,6.62 (d, IH, J = 8.0 Hz, Ar-H), 6.91 (s, IH, Ar-H), 7.14 (d, J = 8.0 Hz, IH 5 Ar-H), 10.72 (br.
IH, NH). IH, NH).
5-Фтop-Ш-индoл-2-илэтилaмин, выход 60%. Спектр 1H ЯМР (400 МГц, DMSO-^6): 2.765-Ftop-III-indol-2-yl-ethylamine, yield 60%. Spectrum 1 H NMR (400 MHz, DMSO- ^ 6 ): 2.76
(уш. с, 2H, CH2-Ar), 2.87 (уш. с, 2H, CH2-N), 6.13 (с, IH5 Ar-H), 6.78-6.81 (м, IH, Ar-H)5 (br s, 2H, CH 2 -Ar), 2.87 (br s, 2H, CH 2 -N), 6.13 (s, IH 5 Ar-H), 6.78-6.81 (m, IH, Ar-H) 5
7.13-7.24 (м, 2H, Ar-H), 10.92 (уш. с, IH, NH). 7.13-7.24 (m, 2H, Ar-H); 10.92 (br s, IH, NH).
5-Xлop-lЯ-индoл-2-илэтилaмин, выход 14%. Спектр 1H ЯМР (400 МГц, DMSO-^6): 1.375-Chlor-lJ-indol-2-yl-ethylamine, yield 14%. 1 H NMR Spectrum (400 MHz, DMSO- ^ 6 ): 1.37
(уш. с, 2H, NH2), 2.87 (д, J = 5.8 Гц, 2H, CH2-Ar), 3.08-3.12 (м, 2H, CH2-N), 6.20 (с, IH, Ar-(br.s, 2H, NH 2 ), 2.87 (d, J = 5.8 Hz, 2H, CH 2 -Ar), 3.08-3.12 (m, 2H, CH 2 -N), 6.20 (s, IH, Ar-
H), 7.08 (д, J= 8.5 Гц, IH, Ar-H)5 7.22 (д, J= 8.5 Гц, IH5 Ar-H)5 7.50 (уш. с, IH5 Ar-H)5 9.40H), 7.08 (d, J = 8.5 Hz, IH, Ar-H) 5 7.22 (d, J = 8.5 Hz, IH 5 Ar-H) 5 7.50 (br.s, IH 5 Ar-H) 5 9.40
(уш. с, IH5 NH). (br.s, IH 5 NH).
Общая методика получения l-мeтил-2,3,4,5-тeтpaгидpo-lЯ-пиpидинo[4,3-Z>]индoлoвGeneral procedure for the preparation of l-methyl-2,3,4,5-tetrahydro-lH-pyridino [4,3-Z>] indoles
К охлажденному до 0 0C раствору 56.2 ммоль полученного выше амина в 50 мл толуола прибавляли при перемешивании 3.37 мл (1.07 экв, 62 ммоль) свежеперегнанного ацетальдегида, перемешивали 15 мин, добавляли 50 мл уксусной кислоты и оставляли на To a solution of 56.2 mmol of the amine obtained above in 50 ml of toluene cooled to 0 ° C, 3.37 ml (1.07 eq, 62 mmol) of freshly distilled acetaldehyde was added with stirring, stirred for 15 min, 50 ml of acetic acid was added and left on
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) ночь. Затем растворители тщательно упаривали, остаток обрабатывали холодной водой, подщелачивали нас. раствором аммиака и экстрагировали хлористым метиленом (3*50 мл). Экстракт сушили над поташом, упаривали и очищали методом колоночной хроматографии (элюент - CH2C12/MeOH 3/1). SUBSTITUTE SHEET (RULE 26) night. Then the solvents were carefully evaporated, the residue was treated with cold water, alkalized us. ammonia solution and was extracted with methylene chloride (3 * 50 ml). The extract was dried over potash, evaporated and purified by column chromatography (eluent — CH2C12 / MeOH 3/1).
l-Meтил-2,354,5-тeтpaгидpo-l//-пиpидинo[4,3-6]индoл, выход 67%, Тпл. 152-154 С. Спектр 1H ЯМР (400 МГц, ДMCO-d6): 1.39 (д, 7.4 Гц, ЗН, CH3-CH), 2.57-2.69 (м, 2H), 2.84- 2.88 (м, IH), 3.13-3.16 (м, IH), 4.08 (кв, 7.4 Гц, IH, CH3-CH ), 6.89-6.99 (м, 2H, Ar-H), 7.25 (д, J= 6.9 Гц, IH, Ar-H), 7.40 (д, J= 7.1 Гц, IH, Ar-H), 10.71 (уш. с, IH, NH). l-Methyl-2,3 5 4,5-tetrahydro-l // - pyridino [4,3-6] indole, yield 67%, mp. 152-154 C. Spectrum 1 H NMR (400 MHz, DMSO-d 6 ): 1.39 (d, 7.4 Hz, 3H, CH 3 -CH), 2.57-2.69 (m, 2H), 2.84- 2.88 (m, IH ), 3.13-3.16 (m, IH), 4.08 (q, 7.4 Hz, IH, CH 3 -CH), 6.89-6.99 (m, 2H, Ar-H), 7.25 (d, J = 6.9 Hz, IH, Ar-H), 7.40 (d, J = 7.1 Hz, IH, Ar-H), 10.71 (br.s, IH, NH).
l-Meтил-2,3>4,5-тeтpaгидpo-l/У-пиpидинo[4,3-^]индoл, выход 87%. Спектр H ЯМР (400l-Methyl-2,3 > 4,5-tetrahydro-l / Y-pyridino [4.3 - ^] indole, 87% yield. H NMR Spectrum (400
МГц, ДMCO-d6): 1.37 (д, 6.4 Гц, ЗН, CH3-CH), 2.33 (с, ЗН, CH3-Ar), 2.55-2.65 (м, 2H), 2.81- 2.87 (м, IH), 3.10-3.14 (м, IH), 4.05 (q, 6.4 Гц, IH, CH3-CH ), 6.78 (д, IH, J= 8.0 Гц, Ar-H), 7.12 (д, IH5 J= 8.0 Гц, Ar-H), 7.16 (с, IH, Ar-H), 10.55 (уш. с, IH3 NH). MHz, DMSO-d 6 ): 1.37 (d, 6.4 Hz, ЗН, CH 3 -CH), 2.33 (s, ЗН, CH 3 -Ar), 2.55-2.65 (m, 2H), 2.81- 2.87 (m, IH), 3.10-3.14 (m, IH), 4.05 (q, 6.4 Hz, IH, CH 3 -CH), 6.78 (d, IH, J = 8.0 Hz, Ar-H), 7.12 (d, IH 5 J = 8.0 Hz, Ar-H), 7.16 (s, IH, Ar-H), 10.55 (br.s, IH 3 NH).
8-Meтoкcи-l-мeтил-2,3,4,5-тeтpaгидpo-l//-пиpидинo[4,3-A]индoл, выход 76%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.37 (д, 6.6 Гц, ЗН, CH3-CH), 2.56-2.60 (м, 2H), 2.82-2.86 (м, IH), 3.08-3.12 (м, IH), 3.72 (с, ЗН, CH3O), 4.0§ (q, 6.6 Гц, IH, CH3-CH ), 6.62 (д, IH, J= 8.4 Гц, Ar-H), 6.86 (с, IH, Ar-H), 7.13 (д, J= 8.4 Гц, IH, Ar-H), 10.52 (уш. с, IH, NH). 8-Methoxy-l-methyl-2,3,4,5-tetrahydro-l // - pyridino [4,3-A] indole, yield 76%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.37 (d, 6.6 Hz, 3H, CH 3 -CH), 2.56-2.60 (m, 2H), 2.82-2.86 (m, IH), 3.08-3.12 (m , IH), 3.72 (s, 3H, CH 3 O), 4.0§ (q, 6.6 Hz, IH, CH 3 -CH), 6.62 (d, IH, J = 8.4 Hz, Ar-H), 6.86 (s , IH, Ar-H), 7.13 (d, J = 8.4 Hz, IH, Ar-H), 10.52 (br.s, IH, NH).
8-Xлop-l-мeтил-2,3,4,5-тeтpaгидpo-lЯ-пиpидинo[4,3-6]индoл, выход 96%. Спектр 1H ЯМР (400 МГц, DMSO-rfβ): 1.54 (д, 6.5 Гц, ЗН, CH3-CH), 2.66-2.76 (м, 2H), 3.07-3.11 (м, IH), 3.34-3.38 (м, IH), 4.26 (q, 6.5 Гц, IH, CH3-CH ), 7.08 (д, J= 8.6 Гц, IH, Ar-H), 7.22 (д, J8-Chlor-l-methyl-2,3,4,5-tetrahydro-lH-pyridino [4.3-6] indole, yield 96%. 1 H NMR spectrum (400 MHz, DMSO-rf β ): 1.54 (d, 6.5 Hz, 3H, CH 3 -CH), 2.66-2.76 (m, 2H), 3.07-3.11 (m, IH), 3.34-3.38 (m, IH), 4.26 (q, 6.5 Hz, IH, CH 3 -CH), 7.08 (d, J = 8.6 Hz, IH, Ar-H), 7.22 (d, J
= 8.6 Гц, IH, Ar-H), 7.48 (уш. с, IH, Ar-H), 7.91 (уш. с, IH, NH). = 8.6 Hz, IH, Ar-H), 7.48 (br.s, IH, Ar-H), 7.91 (br.s, IH, NH).
8-Фтop-l-мeтил-2,3,4,5-тeтpaгидpo-l#-пиpидинo[4,3-£]индoл, выход 98%. Спектр 1H8-Ftop-l-methyl-2,3,4,5-tetrahydro-l # -pyridino [4.3- £] indole, yield 98%. Spectrum 1 H
ЯМР (400 МГц, DMSO-^6): 1.37 (д, 6.4 Гц, ЗН, CH3-CH), 2.59-2.66 (м, 2H), 2.81-2.86 (м, IH), 3.10-3.14 (м, IH), 4.05 (к, 6.4 Гц, IH, CH3-CH ), 6.77-6.81 (м, IH, Ar-H), 7.11-7.25 (м, 2H, Ar-H), 10.84 (уш. с, IH, NH). NMR (400 MHz, DMSO- ^ 6 ): 1.37 (d, 6.4 Hz, 3H, CH 3 -CH), 2.59-2.66 (m, 2H), 2.81-2.86 (m, IH), 3.10-3.14 (m, IH), 4.05 (q, 6.4 Hz, IH, CH 3 -CH), 6.77-6.81 (m, IH, Ar-H), 7.11-7.25 (m, 2H, Ar-H), 10.84 (br.s, IH, NH).
Общая методика получения l-мeтил-l,3,4,5-тeтpaгидpo-l//-пиpидинo[4,3-6]индoл-2- карбальдегидов General procedure for the preparation of l-methyl-l, 3,4,5-tetrahydro-l // - pyridino [4,3-6] indole-2-carbaldehydes
Полученный выше амин (37 ммоль) растворяют при нагревании в 100 мл этилформиата и кипятят 7 ч, затем добавляют 5 мл триэтиламина и снова кипятят 2 'ч. После тщательного упаривания остаток растворяют в хлористом метилене и пропускают через короткую колонку с силикагелем, снова упаривают.  The amine (37 mmol) obtained above is dissolved in 100 ml of ethyl formate with heating and boiled for 7 hours, then 5 ml of triethylamine are added and again boiled for 2 hours. After thorough evaporation, the residue is dissolved in methylene chloride and passed through a short column of silica gel, evaporated again.
l-Meтил-l,3,4,5-тeтpaгидpo-li/-пиpидинo[4,3-6]индoл-2-кapбaльдeгид, выход 88% (-1/1 смесь циc-/тpaнc- амидов). Спектр 1H ЯМР (400 МГц, ДMCO-d6): 1.56 (д, 7.4 Гц, ЗН, CH3-CH, цис- или транс- амид), 1.63 (д, 7.2 Гц, ЗН, CH3-CH, цис- или транс- амид), 2.70- 2.82 (м, 2H, цис- и транс- амид), 2.95-3.02 (м, 2H, цис- и транс- амид), 3.19-3.24 (м, IH, м, l-Methyl-l, 3,4,5-tetrahydro-li / -pyridino [4.3-6] indol-2-carbaldehyde, 88% yield (-1/1 mixture of cis / trans amides). 1 H NMR spectrum (400 MHz, DMSO-d 6 ): 1.56 (d, 7.4 Hz, 3H, CH 3 -CH, cis or trans amide), 1.63 (d, 7.2 Hz, 3H, CH 3 -CH, cis or trans amide), 2.70- 2.82 (m, 2H, cis and trans amide), 2.95-3.02 (m, 2H, cis and trans amide), 3.19-3.24 (m, IH, m,
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) IH, цис- или транс- амид), и 3.64-3.73 (м, IH, цис- или транс- амид), 3.76-3.83 (м, IH, цис- или транс- амид), 4.70-4.75 (м, IH, цис- или транс- амид), 5.01 (кв, 7.4 Гц, IH, CH3-CH1 цис- или транс- амид), 5.71 (кв, 7.2 Гц, IH, CH3-CR1 цис- или транс- амид), 7.10-7.18 (м, 4H, Ar-H, цис- и транс- амид), 7.32-7.31 (м, 2H, Ar-H, цис- и транс- амид), 7.46-7.50 (м, 2H, Ar-H, цис- и транс- амид), 8.03 (уш. с, IH, NH, цис- или транс- амид), 8.07 (уш. с, IH, NH, цис- или транс- амид), 8.19 (с, IH, C(O)H, цис- или транс- амид), 8.39 (с, IH, C(O)H, цис- или транс- амид). SUBSTITUTE SHEET (RULE 26) IH, cis or trans amide), and 3.64-3.73 (m, IH, cis or trans amide), 3.76-3.83 (m, IH, cis or trans amide), 4.70-4.75 (m, IH , cis or trans amide), 5.01 (q, 7.4 Hz, IH, CH 3 -CH 1 cis or trans amide), 5.71 (q, 7.2 Hz, IH, CH 3 -CR 1 cis or trans amide), 7.10-7.18 (m, 4H, Ar-H, cis and trans amide), 7.32-7.31 (m, 2H, Ar-H, cis and trans amide), 7.46-7.50 (m, 2H , Ar-H, cis and trans amide), 8.03 (br.s, IH, NH, cis or trans amide), 8.07 (br., IH, NH, cis or trans amide), 8.19 (s, IH, C (O) H, cis or trans amide), 8.39 (s, IH, C (O) H, cis or trans amide).
l,8-Димeтил-l,354,5-тeтpaгидpo-lH-пиpидинo[4,3-6]индoл-2-кapбaльдeгид, выход 98%. Спектр 1H ЯМР (-1/1 смесь циc-/тpaнc- амидов, 400 МГц, CDCl3): 1.55 (д, 6.5 Гц, ЗН, CH3- CH, цис- или транс-) апd 1.62 (д, 6.8 Гц, ЗН, CH3-CH, цис- или транс-), 2.46 (с, ЗН, CH3- Ar, цис- или транс-), 2.47 (с, ЗН, CH3-Ar, цис- или транс-), 2.68-2.78 (м, 2H, сis- апd trапs- ), 2.89-2.99 (м, 2H, цис- и транс-), 3.18-3.24 (м, IH, цис- или транс-), 3.65-3.79 (м, 2H, цис- и транс-), 4.67-4.72 (м, IH, цис- или транс-), 4.96 (q, 6.8 Гц, IH, CH3-CH1 цис- или транс-), 5.68 (q, 6.5 Гц, IH, CH3-CH1 цис- или транс-), 6.98-7.02 (м, 2H, Ar-H, цис- и транс-), 7.19-7.26 (м, 4H, Ar-H, цис- и транс-), 8.05 (уш. с, IH, NH, цис- или транс-), 8.11 (уш. с, IH, NH, цис- или транс-), 8.18 (с, IH, C(O)H, цис- или транс-), 8.37 (с, IH, C(O)H, цис- или транс-). l, 8-Dimethyl-l, 3 5 4,5-tetrahydro-lH-pyridino [4,3-6] indol-2-carbaldehyde, yield 98%. 1 H NMR Spectrum (-1/1 mixture of cis / trans amides, 400 MHz, CDCl 3 ): 1.55 (d, 6.5 Hz, 3H, CH 3 - CH, cis or trans) add 1.62 (d, 6.8 Hz, ZN, CH 3 -CH, cis or trans), 2.46 (s, Z, CH 3 - Ar, cis or trans), 2.47 (s, ZN, CH 3 -Ar, cis or trans ), 2.68-2.78 (m, 2H, CIS-APD traps-), 2.89-2.99 (m, 2H, CIS and TRANS), 3.18-3.24 (m, IH, CIS or TRANS), 3.65-3.79 (m, 2H, cis and trans), 4.67-4.72 (m, IH, cis or trans), 4.96 (q, 6.8 Hz, IH, CH 3 -CH 1 cis or trans), 5.68 ( q, 6.5 Hz, IH, CH 3 -CH 1 cis or trans), 6.98-7.02 (m, 2H, Ar-H, cis and trans), 7.19-7.26 (m, 4H, Ar-H, cis and trans), 8.05 (broad s, IH, NH, cis or trans), 8.11 (broad s, IH, NH, cis or trans), 8.18 (s, IH, C (O ) H, cis or trans), 8.37 (s, IH, C (O) H, cis or trans).
l,8-Димeтил-l,354,5-тeтpaгидpo-lH-πиpидинo[4,3-^]индoл-2-кapбaльдeгид, выход 97%. Спектр 1H ЯМР (-1/1 смесь циc-/тpaнc- амидов, 400 МГц, CDCl3): 1.36 (д, 6.6 Гц, ЗН, CH3- CH, цис- или транс-) апd 1.48 (д, 6.6 Гц, ЗН, CH3-CH, цис- или транс-), 2.69-2.85 (м, 2H, цис- и транс-), 3.08-3.13 (м, IH, цис- или транс-), 3.52-3.56 (м, 2H, цис- и транс-), Ъ.IА (с, 6H, CH3-O, цис- и транс-), 3.86-3.89 (м, 2H, CH3-O, цис- и транс-), 4.42-4.46 (м, IH, цис- или транс-), 5.01 (q, 6.6 Гц, IH, CH3-CH1 цис- или транс-), 5.41 (q, 6.6 Гц, IH, CH3- CH, цис- или транс-), 6.65-6.67 (м, 2H, Ar-H, цис- и транс-), 6.89 (с, Ar-H, цис- или транс-), 6.93 (с, Ar-H, цис- или транс-), 7.15-7.18 (м, 2H, Ar-H, цис- и транс-), 8.12 (с, IH, C(O)H, цис- или транс-), 8.32 (с, IH, C(O)H, цис- или транс-), 10.71 (уш. с, IH, NH, цис- или транс-), 10.74 (уш. с, IH, NH, цис- или транс-). l, 8-Dimethyl-l, 3 5 4,5-tetrahydro-lH-π-pyridino [4,3 - ^] indol-2-carbaldehyde, yield 97%. 1 H NMR spectrum (-1/1 mixture of cis / trans amides, 400 MHz, CDCl 3 ): 1.36 (d, 6.6 Hz, 3H, CH 3 - CH, cis or trans) add 1.48 (d, 6.6 Hz, ZN, CH 3 -CH, cis or trans), 2.69-2.85 (m, 2H, cis and trans), 3.08-3.13 (m, IH, cis or trans), 3.52-3.56 ( m, 2H, cis and trans), b. IA (s, 6H, CH 3 -O, cis and trans), 3.86-3.89 (m, 2H, CH 3 -O, cis and trans) , 4.42-4.46 (m, IH, cis or trans), 5.01 (q, 6.6 Hz, IH, CH 3 -CH 1 cis or trans), 5.41 (q, 6.6 Hz, IH, CH 3 - CH , cis or trans), 6.65-6.67 (m, 2H, Ar-H, cis and trans), 6.89 (s, Ar-H, cis or trans), 6.93 (s, Ar-H, cis or trans), 7.15-7.18 (m, 2H, Ar-H, cis and trans), 8.12 (s, IH, C (O) H, cis or trans), 8.32 (s, IH , C (O) H, cis or trans), 10.71 (br.s, IH, NH, cis or trans), 10.74 (br. , IH, NH, cis or trans).
8-Xлop-l-мeтил-l,3,4,5-тeтpaгидpo-lH-πиpидинo[4,3-6]индoл-2-кapбaльдeгид, выход 89%. Спектр 1H ЯМР (-1/1 смесь сis- и trапs- амидов, 400 МГц, DМSОчfc): 1.53 (д, 6.5 Гц, ЗН, CH3-CH, сis- или trапs- амиды) и 1.63 (д, 7.0 Гц, ЗН, CH3-CH, сis- или trапs- амиды), 2.71-2.80 (м, 2H, сis- и trапs-), 2.94-3.01 (м, 2H, сis- и trапs- амиды), 3.18-3.22 (м, IH, м, IH, сis- или trапs-), и 3.64-3.70 (м, IH, сis- или trапs-), 3.75-3.82 (м, IH, сis- или trапs-), A.12- А.ll (м, IH, сis- или trапs-), 5.00 (кв, 6.5 Гц, IH, CH3-CH1 сis- или trапs- амиды), 5.70 (кв, 7.0 Гц, IH, CH3-CH1 сis- или trапs- амиды), 7.06-7.22 (м, 4H, Ar-H, сis- и trапs-), 7.50 (уш. s 8-Chlor-l-methyl-l, 3,4,5-tetrahydro-lH-π-pyridino [4.3-6] indol-2-carbaldehyde, 89% yield. 1 H NMR spectrum (-1/1 mixture of cis and traps amides, 400 MHz, DMSOchfc): 1.53 (d, 6.5 Hz, 3H, CH 3 -CH, cis or traps amides) and 1.63 (d, 7.0 Hz, 3H, CH 3 -CH, cis or traps amides), 2.71-2.80 (m, 2H, cis and traps-), 2.94-3.01 (m, 2H, cis and traps amides), 3.18- 3.22 (m, IH, m, IH, cis- or traps-), and 3.64-3.70 (m, IH, cis- or traps-), 3.75-3.82 (m, IH, cis- or traps-), A. 12- A.ll (m, IH, cis or traps-), 5.00 (q, 6.5 Hz, IH, CH 3 -CH 1 cis or traps amides), 5.70 (q, 7.0 Hz, IH, CH 3 -CH 1 cis- or traps-amides), 7.06-7.22 (m, 4H, Ar-H, cis- and traps-), 7.50 (br.s
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 2H, Ar-H, ей- и trапs-), 8.02 (уш. с, IH, NH, ей- или trапs-), 8.06 (уш. с, IH, NH, ей- или trапs-), 8.20 (с, IH, C(O)H, ей- или trапs-), 8.4p (с, IH, C(O)H, ей- или trапs-). SUBSTITUTE SHEET (RULE 26) 2H, Ar-H, her- and traps-), 8.02 (br.s, IH, NH, her- or traps-), 8.06 (br., IH, NH, her- or traps-), 8.20 (s , IH, C (O) H, her or traps-), 8.4p (s, IH, C (O) H, her or traps-).
8-Фтop-l-мeтил-l,3,4,5-тeтpaгидpo-lH-пиpидинo[4,3-6]индoл-2-кapбaльдeгид, выход 86%. Спектр 1H ЯМР (-1/1 miхturе оf ей- апd trапs- аmidеs, 400 МГц, DMSO-J6): 1-53 (d, 6.6 Гц, ЗН, CH3-CH, сis- ог trапs-) апd 1.60 (d, 6.8 Гц, ЗН, CH3-CH, сis- оr trапs- ), 2.73-2.82 (m, IH, сis- апd trапs-), 2.95-2.97 (m, IH, сis- апd trапs- ), 3.00-3.20 (m, IH, сis- ог trапs-) апd 3.68-3.70 (m, IH, сis- оr tгаrø-), 3.79-3.84 (m, IH, сis- оr trапs-), 4.70-4.75 (m, IH, с/5- оr trапs-), 4.96 (q, 6.8 Гц, IH, CH3-CH2 сis- оr trапs- аmidеs), 5.65 (q, 6.6 Гц, IH, CH3-CH2 сis- оr trапs- аmidеs), 6.90-6.92 (m, 2H, Ar-H, сis- апd trапs-), 7.09-7.11 (m, 2H, Ar-H, сis- апd trапs-), 7.22-7.25 (m, 2H, Ar-H, ей- апd trапs-), 7.97 (br. s, IH, NH, сis- оr trапs-), 8.04 (br. s, IH, NH, ей- оr trапs-), 8.19 (s, IH, C(O)H, ей- оr trапs-), 8.38 (s, IH, C(O)H, ей- оr trапs-). 8-Ftop-l-methyl-l, 3,4,5-tetrahydro-lH-pyridino [4,3-6] indol-2-carbaldehyde, yield 86%. 1 H NMR spectrum (-1/1 mihture оf her-add traps-amides, 400 MHz, DMSO-J 6 ): 1-53 (d, 6.6 Hz, 3H, CH 3 -CH, cis-tr trps-) apd 1.60 (d, 6.8 Hz, 3H, CH 3 -CH, cis-tr traps-), 2.73-2.82 (m, IH, cis-trps-), 2.95-2.97 (m, IH, cis-trps-) , 3.00-3.20 (m, IH, cis-oh traps-) app 3.68-3.70 (m, IH, cis-ore targar-), 3.79-3.84 (m, IH, cis-oh traps-), 4.70-4.75 ( m, IH, s / 5- or traps-), 4.96 (q, 6.8 Hz, IH, CH 3 -CH 2 sis-or trs-amides), 5.65 (q, 6.6 Hz, IH, CH 3 -CH 2 cis - or traps-amides), 6.90-6.92 (m, 2H, Ar-H, CIS-APD traps-), 7.09-7.11 (m, 2H, Ar-H, CIS-APD traps-), 7.22-7.25 (m , 2H, Ar-H, her- ap traps-), 7.97 (br. S, IH, NH, CIS- or traps-), 8.04 (br. S, IH, NH, her-traps-), 8.19 ( s, IH, C (O) H, her-traps-), 8.38 (s, IH, C (O) H, her-traps-).
Общая методика получения l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидинo[4,3- b] индолов General Procedure for the Preparation of l, 2-Dimethyl-2,3,4,5-tetrahydro-lH-pyridino [4,3-b] indoles
К суспензии 5 г (4 экв, 0.13 моль) литийалюмогидрида в кипящем абсолютном ТГФ (250 мл) при интенсивном перемешивании медленно в течение 1 ч прибавляли по каплям раствор в 50 мл абсолютного ТГФ 0.032 моль полученного выше формамида. По окончании прибавления реакцилнную смесь кипятили дополнительные 3 ч, охлаждали, разлагали прибавлением 15 мл 10% водного раствора гидроксида натрия, фильтровали, остаток промывали горчим ТГФ (2*50 мл), объединенный экстракт упаривали о очищали методом колоночной хроматографии (элюент - CH2C12/MeOH 3/1).  To a suspension of 5 g (4 equiv, 0.13 mol) of lithium aluminum hydride in boiling absolute THF (250 ml) with vigorous stirring, a solution of 50 ml of absolute THF 0.032 mol of the formamide obtained above was slowly added dropwise over 1 h. Upon completion of the addition, the reaction mixture was boiled for an additional 3 h, cooled, decomposed by the addition of 15 ml of a 10% aqueous solution of sodium hydroxide, filtered, the residue was washed with hot THF (2 * 50 ml), the combined extract was evaporated and purified by column chromatography (eluent - CH2C12 / MeOH 3/1).
l,2-Димeтил-2,3,4,5-тeтpaгидpo-l//-пиpидинo[4,3-6]индoл, выход 67%, Тпл. 127-128 С. Спектр 1H ЯМР (400 МГц, CDC13): 1.54 (д, 7.6 Гц, ЗН, CH3-CH), 2.57 (с, ЗН, CH3-N), 2.71- 2.79 (м, ЗН), 3.09-3.13 (м, IH), 3.87 (кв, 7.6 Гц, IH, CH3-CH ), 7.08-7.15 (м, 2H, Ar-H), 7.25 (д, J= 7.0 Гц, IH, Ar-H), 7.52 (д, J= 7.4 Гц, IH, Ar-H), 8.25 (уш. с, IH, NH). l, 2-Dimethyl-2,3,4,5-tetrahydro-l // - pyridino [4,3-6] indole, yield 67%, mp. 127-128 С. Spectrum 1 H NMR (400 MHz, CDC13): 1.54 (d, 7.6 Hz, ЗН, CH 3 -CH), 2.57 (s, ЗН, CH 3 -N), 2.71- 2.79 (m, ЗН) ), 3.09-3.13 (m, IH), 3.87 (q, 7.6 Hz, IH, CH 3 -CH), 7.08-7.15 (m, 2H, Ar-H), 7.25 (d, J = 7.0 Hz, IH, Ar-H), 7.52 (d, J = 7.4 Hz, IH, Ar-H), 8.25 (br.s, IH, NH).
l,2,8-Tpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидинo [4,3-6] индол, выход 85%, Спектр 1H ЯМР (400 МГц, CDCl3): 1.53 (д, J= 6.5 Гц, ЗН, CH3-CH), 2.47 (с, ЗН, CH3-Ar), 2.57 (с, ЗН, CH3-N), 2.74-2.80 (м, ЗН), 3.12-3.16 (м, IH), 3.82 (q, J= 6.5 Гц, IH, CH3-CH ), 6.96 (д, J = 8.1 Гц, IH, Ar-H), 7.15 (д, J= 8.1 Гц, IH, Ar-H), 7.30 (с, IH, Ar-H), 8.03 (уш. с, IH, NH). 8-Meтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидинo[4,3-6]индoл, выход 58%. Спектр IH ЯМР (400 МГц, CDCl3): 1.50 (д, J = 6.5 Гц, ЗН, CH3-CH), 2.56 (с, ЗН, CH3-N), 2.78-2.80 (м, ЗН), 3.11-3.15 (м, IH), 3.81 (q, J = 6.5 Гц, IH, CH3-CH ), 3.87 (с, ЗН, CH3O), 6.79 (д, J = 8.6 Гц, IH, Ar-H), 6.97 (с, IH, Ar-H), 7.16 (д, J = 8.6 Гц, IH, Ar-H), 7.89 (уш. с, IH, NH). l, 2,8-Trimethyl-2,3,4,5-tetrahydro-III-pyridino [4.3-6] indole, 85% yield, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.53 (d, J = 6.5 Hz, 3H, CH 3 -CH), 2.47 (s, 3H, CH 3 -Ar), 2.57 (s, 3H, CH 3 -N), 2.74-2.80 (m, 3H), 3.12-3.16 ( m, IH), 3.82 (q, J = 6.5 Hz, IH, CH 3 -CH), 6.96 (d, J = 8.1 Hz, IH, Ar-H), 7.15 (d, J = 8.1 Hz, IH, Ar -H), 7.30 (s, IH, Ar-H), 8.03 (br s, IH, NH). 8-Methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyridino [4.3-6] indole, 58% yield. 1H NMR spectrum (400 MHz, CDCl 3 ): 1.50 (d, J = 6.5 Hz, 3H, CH 3 -CH), 2.56 (s, 3H, CH 3 -N), 2.78-2.80 (m, 3H), 3.11 -3.15 (m, IH), 3.81 (q, J = 6.5 Hz, IH, CH 3 -CH), 3.87 (s, 3Н, CH 3 O), 6.79 (d, J = 8.6 Hz, IH, Ar-H ), 6.97 (s, IH, Ar-H), 7.16 (d, J = 8.6 Hz, IH, Ar-H), 7.89 (br.s, IH, NH).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 8-Xлop-l,2-димeтил-2,3,4,5-тeтpaгидpo-lЯ-пиpидинo[4,3-*]индoл, выход 68%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.49 (д, 6.5 Гц, ЗН, CH3-CH), 2.56 (с, ЗН, CH3-N), 2.73-2.80 (м, 3H), 3.08-3.12 (м, IH), 3.86 (кв, 6.5 Гц, IH, CH3-CH ), 7.02 (дд, J = 8.6 и 2.0 Гц, IH, Ar-H), 7.11 (д, J= 8.6 Гц, IH, Ar-H), 7.41 (д, J= 2.0 Гц, IH, Ar-H), 8.75 (уш. с, IH, NH). SUBSTITUTE SHEET (RULE 26) 8-Chlor-l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyridino [4.3 - *] indole, 68% yield. 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.49 (d, 6.5 Hz, 3H, CH 3 -CH), 2.56 (s, 3H, CH 3 -N), 2.73-2.80 (m, 3H), 3.08- 3.12 (m, IH), 3.86 (q, 6.5 Hz, IH, CH 3 -CH), 7.02 (dd, J = 8.6 and 2.0 Hz, IH, Ar-H), 7.11 (d, J = 8.6 Hz, IH , Ar-H), 7.41 (d, J = 2.0 Hz, IH, Ar-H), 8.75 (br.s, IH, NH).
8-Фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидинo[4,3-ό]индoл, выход 68%. Спектр 1H ЯМР (400 МГц, CDCl3): IH NMR (400 МГд, DMSO-D6) 1.53 (д, J = 6.6 Гц, ЗН, CH3-CH ) 2.62 (с, ЗН, CH3-N) 2.85-2.88 (м, 2H) 2.89-2.96 (м, 1 H) 3.22-3.25 (м, IH) 4.02 (к, J= 6.6 Гц, IH) 6.84-6.90 (м, IH, Ar-H) 7.08 (дд, J = 8.7 и 2.2 Гц, IH, Ar-H) 7.16 (дд, J = 8.7 и 4.4 Гц, IH, Ar-H) 8.48 (с, IH, NH). 8-Ftop-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyridino [4,3-ό] indole, 68% yield. 1 H NMR Spectrum (400 MHz, CDCl 3 ): IH NMR (400 MHD, DMSO-D6) 1.53 (d, J = 6.6 Hz, 3H, CH 3 -CH) 2.62 (s, 3H, CH 3 -N) 2.85 -2.88 (m, 2H) 2.89-2.96 (m, 1 H) 3.22-3.25 (m, IH) 4.02 (q, J = 6.6 Hz, IH) 6.84-6.90 (m, IH, Ar-H) 7.08 (dd , J = 8.7 and 2.2 Hz, IH, Ar-H) 7.16 (dd, J = 8.7 and 4.4 Hz, IH, Ar-H) 8.48 (s, IH, NH).
Общая методика получения l,2-димeтил-2,3>4,5-тeтpaгидpo-l//-пиpидинo[4,3-General procedure for the preparation of l, 2-dimethyl-2,3 > 4,5-tetrahydro-l // - pyridino [4,3-
Z>] индолов через 7V-[2-(liУ-индoл-2-ил)этил]-7V-мeтилaмины Общая методика получения 2-(l/У-индoл-2-ил)этилфopмaмидoв lH-индoл-2-илэтилaмины (63 ммоль) растворяют при нагревании в 150 мл этилформиата и кипятят 7 ч, затем добавляют 5 мл триэтиламина и снова кипятят 2 ч. После тщательного упаривания остаток растворяют в хлористом метилене и пропускают через короткую колонку с силикагелем, снова упаривают. Z>] indoles via 7V- [2- (liY-indol-2-yl) ethyl] -7V-methylamines General Procedure for the Preparation of 2- (l / Y-indol-2-yl) ethylformamides lH-indol-2-yl-ethylamines ( 63 mmol) was dissolved in 150 ml of ethyl formate with heating and boiled for 7 hours, then 5 ml of triethylamine was added and again boiled for 2 hours. After thorough evaporation, the residue was dissolved in methylene chloride and passed through a short column of silica gel, evaporated again.
2-(lЯ-индoл-2-ил)этилфopмaмид, выход 86%, спектр 1H ЯМР (400 МГц, CDC13): 3.03 (t, 2H, J= 7.4 Гц, CH2-Ar), 3.65-3.70 (м, 2H, CH2-N), 6.31 (с, IH, Ar-H), 7.08-7.18 (м, 2H, Ar- H), 7.34 (д, J= 6.9 Гц, IH, Ar-H), 7.55 (д, J= 7.2 Гц, IH, Ar-H), 8.15 (с, IH, C(O)H), 8.30 (уш. с, IH5 NH). 2- (lH-indol-2-yl) ethyl formamide, 86% yield, 1 H NMR spectrum (400 MHz, CDC13): 3.03 (t, 2H, J = 7.4 Hz, CH 2 -Ar), 3.65-3.70 (m , 2H, CH 2 -N), 6.31 (s, IH, Ar-H), 7.08-7.18 (m, 2H, Ar-H), 7.34 (d, J = 6.9 Hz, IH, Ar-H), 7.55 (d, J = 7.2 Hz, IH, Ar-H), 8.15 (s, IH, C (O) H), 8.30 (br s, IH 5 NH).
2-(5-Meтил-lД-индoл-2-ил)этилфopмaмид, выход 99%, в виде коричневого вязкого масла, медленно кристаллизующегося при стоянии. Спектр H ЯМР (400 МГц, CDCl3): 2.32 (с, ЗН, CH3-Ar), 2.84 (t, 2H, J= 7.1 Гц, CH2-Ar), 3.42 (t, 2H, J= 7.1 Гц, CH2-N), 6.08 (с, IH, Ar-H), 6.81 (д, IH, J = 8.0 Гц, Ar-H), 7.15 (д, IH, J = 8.0 Гц, Ar-H), 7.18 (с, IH, Ar-H), 8.00 (с, IH, C(O)H), 10.82 (уш. с, IH, NH). 2- (5-Methyl-l-Indol-2-yl) ethyl formamide, yield 99%, as a brown viscous oil, slowly crystallizing upon standing. H NMR spectrum (400 MHz, CDCl 3 ): 2.32 (s, 3H, CH 3 -Ar), 2.84 (t, 2H, J = 7.1 Hz, CH 2 -Ar), 3.42 (t, 2H, J = 7.1 Hz , CH 2 -N), 6.08 (s, IH, Ar-H), 6.81 (d, IH, J = 8.0 Hz, Ar-H), 7.15 (d, IH, J = 8.0 Hz, Ar-H), 7.18 (s, IH, Ar-H), 8.00 (s, IH, C (O) H), 10.82 (br s, IH, NH).
2-(5-Meтoкcи-Ш-индoл-2-ил)этилфopмaмид, выход 99%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.83-2.86 (м, 2H, CH2-Ar), 3.41-3.46 (м, 2H, CH2-N), 3.71 (с, ЗН, CH3O), 6.11 (с, IH, Ar-H), 6.34 (д, IH, J= 8.7 Гц, Ar-H), 6.92(c, IH, Ar-H), 7.14 (д, J= 8.7 Гц, IH, Ar-H), 8.01 (с, IH, C(O)H), 10.80 (уш. с, IH, NH). 2- (5-Methoxy-III-indol-2-yl) ethyl formamide, 99% yield. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 2.83-2.86 (m, 2H, CH 2 -Ar), 3.41-3.46 (m, 2H, CH 2 -N), 3.71 (s, 3H, CH 3 O) , 6.11 (s, IH, Ar-H), 6.34 (d, IH, J = 8.7 Hz, Ar-H), 6.92 (s, IH, Ar-H), 7.14 (d, J = 8.7 Hz, IH, Ar-H), 8.01 (s, IH, C (O) H), 10.80 (br s, IH, NH).
2-(5-Фтop-l//-Индoл-2-ил)этилфopмaмид, выход 99%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.88 (т, J= 7.4 Гц, 2H, CH2-Ar), 3.43-3.46 (м, 2H, CH2-N), 6.19 (с, IH, Ar-H), 6.83 (т, J= 8.9 Гц, IH, Ar-H), 7.17 (д, J- 9.8 Гц, IH, Ar-H) 7.26 (дд, J= 8.2 и 4.4 Гц, IH, Ar-H) 8.13 (с, Ш, NH-фopмил), 8.31 (уш. с, IH5 NH), 11.08 (с, IH, C(O)H). 2- (5-Фтop-l // - Indol-2-yl) ethyl formamide, 99% yield. 1 H NMR spectrum (400 MHz, CDCl 3 ): 2.88 (t, J = 7.4 Hz, 2H, CH 2 -Ar), 3.43-3.46 (m, 2H, CH 2 -N), 6.19 (s, IH, Ar -H), 6.83 (t, J = 8.9 Hz, IH, Ar-H), 7.17 (d, J- 9.8 Hz, IH, Ar-H) 7.26 (dd, J = 8.2 and 4.4 Hz, IH, Ar- H) 8.13 (s, W, NH-formyl), 8.31 (br s, IH 5 NH), 11.08 (s, IH, C (O) H).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Общая методика получения N-[2-(lH-индoл-2-ил)этил]-N-мeтилaминoв SUBSTITUTE SHEET (RULE 26) General Procedure for the Preparation of N- [2- (lH-indol-2-yl) ethyl] -N-methylamines
восстановлением формамидов  formamide recovery
К суспензии 9.5 г (2.7 экв, 0.24 моль) литийалюмогидрида в кипящем абсолютном ТГФ (250 мл) при интенсивном перемешивании медленно в течение 1 ч прибавляли по каплям раствор в 50 мл абсолютного ТГФ 12.5 г (0.063 моль) полученного выше формамида. По окончании прибавления реакционную смесь кипятили дополнительные 3 ч, охлаждали, разлагали прибавлением 15 мл 10% водного раствора гидроксида натрия, фильтровали, остаток промывали горчим ТГФ (2*50 мл), объединенный экстракт упаривали о очищали методом колоночной хроматографии (элюент - CH2C12/MeOH 3/1).  To a suspension of 9.5 g (2.7 equiv, 0.24 mol) of lithium aluminum hydride in boiling absolute THF (250 ml) with vigorous stirring, a solution of 50 ml of absolute THF 12.5 g (0.063 mol) of the formamide obtained above was slowly added dropwise over 1 h. Upon completion of the addition, the reaction mixture was boiled for an additional 3 h, cooled, decomposed by adding 15 ml of a 10% aqueous solution of sodium hydroxide, filtered, the residue was washed with hot THF (2 * 50 ml), the combined extract was evaporated and purified by column chromatography (eluent - CH2C12 / MeOH 3/1).
iV-[2-(5-мeтил-l//-индoл-2-ил)этил]-./V-мeтщiaмин, выход 67%, слабоокрашенное вязкое масло. Спектр 1H ЯМР (400 МГц, CDCl3): 2.43 (s, ЗН, CH3-Ar), 2.49 (s, ЗН, CH3-N), 2.89- 2.95 (m, 4H, CH2-CH2), 6.16 (s, IH, Ar-H), 6.95 (d, IH, J= 8.4 Гц, Ar-H), 7.21 (d, IH, J = 8.4 Гц, Ar-H), 7.32 (s, IH, Ar-H), 9.15 (br. s, IH, NH). IV- [2- (5-methyl-l // - indol-2-yl) ethyl] -. / V-methsamine, yield 67%, slightly colored viscous oil. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 2.43 (s, 3H, CH 3 -Ar), 2.49 (s, 3H, CH 3 -N), 2.89- 2.95 (m, 4H, CH 2 -CH 2 ) 6.16 (s, IH, Ar-H), 6.95 (d, IH, J = 8.4 Hz, Ar-H), 7.21 (d, IH, J = 8.4 Hz, Ar-H), 7.32 (s, IH, Ar-H), 9.15 (br. S, IH, NH).
УV-[2-(5-мeтил-Ш-индoл-2-ил)этил]-7V-мeтилaмин, выход 76%, Спектр 1H ЯМР (400 МГц, CDCl3): 2.43 (с, ЗН, CH3-Ar), 2.49 (с, ЗН, CH3-N), 2.89-2.95 (м, 4H, CH2-CH2), 6.16 (с, IH, Ar-H), 6.95 (д, IH, J = 8.4 Гц, Ar-H), 7.21 (д, IH, J = 8.4 Гц, Ar-H), 7.32 (с, IH, Ar-H), 9.15 (уш. с, IH5 NH). UV- [2- (5-methyl-Ш-indol-2-yl) ethyl] -7V-methylamine, yield 76%, Spectrum 1 H NMR (400 MHz, CDCl 3 ): 2.43 (s, CH, CH 3 - Ar), 2.49 (s, 3H, CH 3 -N), 2.89-2.95 (m, 4H, CH 2 -CH 2 ), 6.16 (s, IH, Ar-H), 6.95 (d, IH, J = 8.4 Hz, Ar-H), 7.21 (d, IH, J = 8.4 Hz, Ar-H), 7.32 (s, IH, Ar-H), 9.15 (br.s, IH 5 NH).
N-[2-(5-мeтoкcи-ljH-индoл-2-ил)этил]-iV-мeтилaмин, выход 92%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.50 (с, ЗН, CH3-N), 2.89-2.96 (м, 4H, CH2-CH2), 3.85 (с, ЗН, CH3O), 6.18 (с, IH, Ar-H), 6.79 (д, IH, J = 8.8 Гц, Ar-H), 7.02 (с, IH, Ar-H), 7.21 (д, J = 8.8 Гц, IH, Ar-H), 9.22 (уш. с, IH, NH). N- [2- (5-Methoxy-ljH-indol-2-yl) ethyl] -iV-methylamine, yield 92%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 2.50 (s, 3H, CH 3 -N), 2.89-2.96 (m, 4H, CH 2 -CH 2 ), 3.85 (s, 3H, CH 3 O), 6.18 (s, IH, Ar-H), 6.79 (d, IH, J = 8.8 Hz, Ar-H), 7.02 (s, IH, Ar-H), 7.21 (d, J = 8.8 Hz, IH, Ar -H), 9.22 (br s, IH, NH).
N-[2-(5-Фтop-Ш-индoл-2-ил)этил]-iV-мeтилaмин, выход 97%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.49 (с, ЗН, CH3-N), 2.95 (м, 4H, CH2-CH2), 6.19 (с, IH, Ar-H), 6.80-6.85 (м, IH, Ar-H), 7.15-7.26 (м, 2H, Ar-H), 8.02 (м, IH, Ar-H), 9.10 (уш. с, 1H,÷NH). N- [2- (5-Ftop-III-indol-2-yl) ethyl] -iV-methylamine, yield 97%. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 2.49 (s, 3H, CH 3 -N), 2.95 (m, 4H, CH 2 -CH 2 ), 6.19 (s, IH, Ar-H), 6.80- 6.85 (m, IH, Ar-H), 7.15-7.26 (m, 2H, Ar-H), 8.02 (m, IH, Ar-H), 9.10 (br.s, 1H, ÷ NH).
Общая методика получения N-[2-(lH-индoл-2-ил)этил]-N-мeтилaминoв General Procedure for the Preparation of N- [2- (lH-indol-2-yl) ethyl] -N-methylamines
метилированием TV- [2-(l//-индoл-2-ил)этил]-Λг-мeтил аминов lH-индoл-2-илэтилaмины (1 ммоль) растворяют в 10 мл ТГФ или метанола и добавляют 1 ммоль метилиодида или диметилсульфата при комнатной температуре перемешивают или нагреванют до 60 0C 2 ч. Добавляют раствор соды или NaOH экстрагируют, упаривают и остаток хроматографируют через короткую колонку с силикагелем, снова упаривают. iV-[2-(5-мeтил-Ш-индoл-2-ил)этил]-iV-мeтилaмин, выход 27%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.43 (с, ЗН, CH3-Ar), 2.49 (с, ЗН, CH3-N), 2.89-2.95 (м, 4H, CH2-CH2), 6.16 (с, IH, Ar-H), 6.95 (д, IH, J = 8.4 Гц, Ar-H), 7.21 (д, IH, J = 8.4 Гц, Ar-U), 7.32 (с, IH, Ar-H), 9.15 (уш. с, IH, NH). methylation of TV- [2- (l // - indol-2-yl) ethyl] -Λ g- methyl amines lH-indol-2-yl-ethylamines (1 mmol) are dissolved in 10 ml of THF or methanol and 1 mmol of methyl iodide or dimethyl sulfate is added at room temperature, it is stirred or heated to 60 ° C. for 2 hours. A solution of soda is added or NaOH is extracted, evaporated and the residue is chromatographed over a short silica gel column, evaporated again. IV- [2- (5-methyl-III-indol-2-yl) ethyl] -iV-methylamine, yield 27%. Spectrum 1 H NMR (400 MHz, CDCl 3 ): 2.43 (s, 3H, CH 3 -Ar), 2.49 (s, 3H, CH 3 -N), 2.89-2.95 (m, 4H, CH 2 -CH 2 ) 6.16 (s, IH, Ar-H), 6.95 (d, IH, J = 8.4 Hz, Ar-H), 7.21 (d, IH, J = 8.4 Hz, Ar-U), 7.32 (s, IH, Ar-H), 9.15 (br s, IH, NH).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 7V-[2-(5-мeтил-lH-индoл-2-ил)этил]-iV-мeтилaмин выход 21%, Спектр H ЯМР (400 МГц, CDCl3): 2.43 (с, ЗН, CH3-Ar), 2.49 (с, ЗН, CH3-N), 2.89-2.95 (м, 4H, CH2-CH2), 6.16 (с, IH, Ar-H), 6.95 (д, IH, J = 8.4 Гц, Ar-H), 7.21 (д, IH, J = 8.4 Гц, Ar-H), 7.32 (с, IH, Ar-H), 9.15 (уш. с, IH, NH). SUBSTITUTE SHEET (RULE 26) 7V- [2- (5-methyl-lH-indol-2-yl) ethyl] -iV-methylamine yield 21%, H NMR spectrum (400 MHz, CDCl 3 ): 2.43 (s, CH, CH 3 -Ar) , 2.49 (s, 3H, CH 3 -N), 2.89-2.95 (m, 4H, CH 2 -CH 2 ), 6.16 (s, IH, Ar-H), 6.95 (d, IH, J = 8.4 Hz, Ar-H), 7.21 (d, IH, J = 8.4 Hz, Ar-H), 7.32 (s, IH, Ar-H), 9.15 (br.s, IH, NH).
iV-[2-(5-мeтoкcи-l//-индoл-2-ил)этил]-iV-мeтилaмин выход 19%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.50 (с, ЗН, CH3-N), 2.89-2.96 (м, 4H, CH2-CH2), 3.85 (с, ЗН, CH3O), 6.18 (с, IH, Ar-H), 6.79 (д, IH, J = 8.8 Гц, Ar-H), 7.02 (с, IH, Ar-H), 7.21 (д,-J = 8.8 Гц, IH, Ar-H), 9.22 (уш. с, IH, NH). IV- [2- (5-methoxy-l // - indol-2-yl) ethyl] -iV-methylamine yield 19%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 2.50 (s, 3H, CH 3 -N), 2.89-2.96 (m, 4H, CH 2 -CH 2 ), 3.85 (s, 3H, CH 3 O), 6.18 (s, IH, Ar-H), 6.79 (d, IH, J = 8.8 Hz, Ar-H), 7.02 (s, IH, Ar-H), 7.21 (d, -J = 8.8 Hz, IH, Ar-H), 9.22 (br s, IH, NH).
N-[2-(5-фтop-l//-индoл-2-ил)этил]-N-мeтилaмин, выход 27%. Спектр 1H ЯМР (400 МГц, CDCl3): 2.49 (с, ЗН, CH3-N), 2.95 (м, 4H, CH2-CH2), 6.19 (с, IH, Ar-H), 6.80-6.85 (м, IH, Ar- H), 7.15-7.26 (м, 2H, Ar-H), 8.02 (м, IH, Ar-H), 9.10 (уш. с, IH, NH). N- [2- (5-ftop-l // - indol-2-yl) ethyl] -N-methylamine, yield 27%. 1 H NMR Spectrum (400 MHz, CDCl 3 ): 2.49 (s, 3H, CH 3 -N), 2.95 (m, 4H, CH 2 -CH 2 ), 6.19 (s, IH, Ar-H), 6.80- 6.85 (m, IH, Ar-H), 7.15-7.26 (m, 2H, Ar-H), 8.02 (m, IH, Ar-H), 9.10 (br.s, IH, NH).
Общая методика циклизации в l,2-димeтил-2,3,4,5-тeтpaгидpo-li/-пиpидинo[4,3- b) индолы General procedure for cyclization in l, 2-dimethyl-2,3,4,5-tetrahydro-li / -pyridino [4,3-b) indoles
К охлажденному до 0 0C раствору 5.62 ммоль полученного выше амина в 5 мл толуола прибавляли при перемешивании 0.337 мл (1.07 экв, 6.2 ммоль) свежеперегнанного ацетальдегида, перемешивали 15 мин, добавляли 50 мл уксусной кислоты и оставляли на ночь. Затем растворители тщательно упаривали, остаток обрабатывали холодной водой, подщелачивали нас. раствором аммиака и экстрагировали хлористым метиленом (3*50 мл). Экстракт сушили над поташом, упаривали и очищали методом колоночной хроматографии (элюент - CH2Cl2/Me0H 3/1). To a solution cooled to 0 ° C, 5.62 mmol of the amine obtained above in 5 ml of toluene was added with stirring 0.337 ml (1.07 eq, 6.2 mmol) of freshly distilled acetaldehyde, stirred for 15 min, 50 ml of acetic acid was added and left overnight. Then the solvents were carefully evaporated, the residue was treated with cold water, alkalized us. ammonia solution and was extracted with methylene chloride (3 * 50 ml). The extract was dried over potash, evaporated and purified by column chromatography (eluent — CH 2 Cl 2 / Me0H 3/1).
l,2-Димeтил-2,3,4,5-тeтpaгидpo-lЯ-пиpидинo[4,3-6]индoл, выход 67%, Тпл. 127-128 С. Спектр 1H ЯМР (400 МГц, CDC13): 1.54 (д, 7.6 Гц, ЗН, CH3-CH), 2.57 (с, ЗН, CH3-N), 2.71- 2.79 (м, ЗН), 3.09-3.13 (м, IH), 3.87 (кв, 7.6 Гц, IH, CH3-CH ), 7.08-7.15 (м, 2H, Ar-H), 7.25 (д, J= 7.0 Гц, IH, Ar-H), 7.52 (д, J= 7.4 Гц, IH, Ar-H), 8.25 (уш. с, IH, NH). l, 2-Dimethyl-2,3,4,5-tetrahydro-l-pyridino [4.3-6] indole, yield 67%, mp. 127-128 С. Spectrum 1 H NMR (400 MHz, CDC13): 1.54 (d, 7.6 Hz, ЗН, CH 3 -CH), 2.57 (s, ЗН, CH 3 -N), 2.71- 2.79 (m, ЗН) ), 3.09-3.13 (m, IH), 3.87 (q, 7.6 Hz, IH, CH 3 -CH), 7.08-7.15 (m, 2H, Ar-H), 7.25 (d, J = 7.0 Hz, IH, Ar-H), 7.52 (d, J = 7.4 Hz, IH, Ar-H), 8.25 (br.s, IH, NH).
l,2,8-Tpимeтил-2,354,5-тeтpaгидpo-l#-пиpидинo[4,3-6]индoл, выход 85%, Спектр 1Hl, 2,8-Trimethyl-2,3 5 4,5-tetrahydro-l # -pyridino [4,3-6] indole, yield 85%, Spectrum 1 H
ЯМР (400 МГц, CDCl3): 1.53 (д, J= 6.5 Гц, ЗН, CH3-CH), 2.47 (с, ЗН, CH3-Ar), 2.57 (с, ЗН, CH3-N), 2.74-2.80 (м, ЗН), 3.12-3.16 (м, IH), 3.82 (q, J= 6.5 Гц, IH, CH3-CH ), 6.96 (д, J = 8.1 Гц, IH, Ar-H), 7.15 (д, J= 8.1 Гц, IH, Ar-H), 7.30 (с, IH, Ar-H), 8.03 (уш. с, IH, NH). 8-Meтoкcи-l,2-димeтил-2,3»4,5-тeтpaгидpo-lH-пиpидинo[4,3-6]индoл, выход 58%. Спектр IH ЯМР (400 МГц, CDCl3): 1.50 (д, J = 6.5 Гц, ЗН, CH3-CH), 2.56 (с, ЗН, CH3-N), 2.78-2.80 (м, ЗН), 3.11-3.15 (м, IH), 3.81 (q, J = 6.5 Гц, IH, CH3-CH ), 3.87 (с, ЗН, CH3O), 6.79 (д, J= 8.6 Гц, IH, Ar-H), 6.97 (с, IH, Ar-H), 7.16 (д, J = 8.6 Гц, IH, Ar-H), 7.89 (уш. с, IH, NH). NMR (400 MHz, CDCl 3 ): 1.53 (d, J = 6.5 Hz, 3H, CH 3 -CH), 2.47 (s, 3H, CH 3 -Ar), 2.57 (s, 3H, CH 3 -N), 2.74-2.80 (m, 3Н), 3.12-3.16 (m, IH), 3.82 (q, J = 6.5 Hz, IH, CH 3 -CH), 6.96 (d, J = 8.1 Hz, IH, Ar-H) 7.15 (d, J = 8.1 Hz, IH, Ar-H), 7.30 (s, IH, Ar-H), 8.03 (br.s, IH, NH). 8-Methoxy-l, 2-dimethyl-2,3 ” 4,5-tetrahydro-lH-pyridino [4,3-6] indole, yield 58%. 1H NMR spectrum (400 MHz, CDCl 3 ): 1.50 (d, J = 6.5 Hz, 3H, CH 3 -CH), 2.56 (s, 3H, CH 3 -N), 2.78-2.80 (m, 3H), 3.11 -3.15 (m, IH), 3.81 (q, J = 6.5 Hz, IH, CH 3 -CH), 3.87 (s, 3Н, CH 3 O), 6.79 (d, J = 8.6 Hz, IH, Ar-H ), 6.97 (s, IH, Ar-H), 7.16 (d, J = 8.6 Hz, IH, Ar-H), 7.89 (br.s, IH, NH).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 8-Xлop-l,2-димeтил-2,3,4,5-тeтpaгидpo-l/)Г-пиpидинo[4,3-^]индoл, выход 61%. Спектр 1H ЯМ? (400 МГц, CDCl3): 1.49 (д, 6.5 Гц, ЗН, CH3-CH), 2.56 (с, ЗН, CH3-N), 2.73-2.80 (м, 3H), 3.08-3.12 (м, IH), 3.86 (кв, 6.5 Гц, IH, CH3-CH ), 7.02 (дд, J = 8.6 и 2.0 Гц, IH, Ar-H), 7.11 (д, J= 8.6 Гц, IH, Ar-H), 7.41 (д, J= 2.0 Гц, IH, Ar-H), 8.75 (уш. с, IH, NH). SUBSTITUTE SHEET (RULE 26) 8-Chlor-l, 2-dimethyl-2,3,4,5-tetrahydro-l /) G-pyridino [4,3 - ^] indole, yield 61%. Spectrum 1 H NM? (400 MHz, CDCl 3 ): 1.49 (d, 6.5 Hz, 3H, CH 3 -CH), 2.56 (s, 3H, CH 3 -N), 2.73-2.80 (m, 3H), 3.08-3.12 (m, IH), 3.86 (q, 6.5 Hz, IH, CH 3 -CH), 7.02 (dd, J = 8.6 and 2.0 Hz, IH, Ar-H), 7.11 (d, J = 8.6 Hz, IH, Ar-H ), 7.41 (d, J = 2.0 Hz, IH, Ar-H), 8.75 (br.s, IH, NH).
8-Фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-lЬГ-пиpидинo[4,3-6]индoл, выход 88%. Спектр 1H ЯМР (400 МГц, CDCl3): IH NMR (400 МГц, DMSO-D6) 1.53 (д, J= 6.6 Гц, ЗН, CH3-CH ) 2.62 (с, ЗН, CH3-N) 2.85-2.88 (м, 2H) 2.89-2.96 (м, 1 H) 3.22-3.25 (м, IH) 4.02 (к, J= 6.6 Гц, IH) 6.84-6.90 (м, IH, Ar-H) 7.08 (дд, J = 8.7 и 2.2 Гц, IH, Ar-H) 7.16 (дд, J = 8.7 и 4.4 Гц, IH, Ar-H) 8.48 (с, IH5 NH). 8-Ftop-l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyridino [4.3-6] indole, 88% yield. 1 H NMR Spectrum (400 MHz, CDCl 3 ): IH NMR (400 MHz, DMSO-D6) 1.53 (d, J = 6.6 Hz, 3H, CH 3 -CH) 2.62 (s, 3H, CH 3 -N) 2.85 -2.88 (m, 2H) 2.89-2.96 (m, 1 H) 3.22-3.25 (m, IH) 4.02 (q, J = 6.6 Hz, IH) 6.84-6.90 (m, IH, Ar-H) 7.08 (dd , J = 8.7 and 2.2 Hz, IH, Ar-H) 7.16 (dd, J = 8.7 and 4.4 Hz, IH, Ar-H) 8.48 (s, IH 5 NH).
Алкилирование 3-фeнилпpoпилбpoмидoм -Alkylation with 3-phenylpropyl bromide -
К раствору 1 моль замещенного индола (синтезированного по вышеприведенным методикам) в 2 мл ДМФА добавляют 120 мг (3 ммоль) NaH при 00C. Смесь выдерживают 30 мин при этой температуре, а затем медленно прикапывают раствор 597 мг (3 ммоль) 3- фенилпропилбромида в 3 мл ДМФА. Смесь перемешивают 12 часов при комнатной температуре. Реакционную смесь разлагают водой, экстрагируют этилацетатом (3*50 мл), сушат над поташом и упаривают в вакууме. Продукт очищают методом колоночной хроматографии (дихлорметан-метанол 4-1). После очистки продукт растворяют в метаноле, пропускают HCl (газ) и упаривают в вакууме. Получают продукт в виде окрашенного твердого вещества. To a solution of 1 mol of substituted indole (synthesized according to the above methods) in 2 ml of DMF was added 120 mg (3 mmol) of NaH at 0 ° C. The mixture was held for 30 minutes at this temperature, and then a solution of 597 mg (3 mmol) of 3- was slowly added. phenylpropyl bromide in 3 ml of DMF. The mixture was stirred for 12 hours at room temperature. The reaction mixture is decomposed with water, extracted with ethyl acetate (3 * 50 ml), dried over potash and evaporated in vacuo. The product is purified by column chromatography (dichloromethane-methanol 4-1). After purification, the product is dissolved in methanol, HCl (gas) is passed and evaporated in vacuo. The product is obtained in the form of a colored solid.
2-Meтoкcи-ll-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 521): Выход 40%. 1H NMR (400 МГц, CDCl3): 1.73-1.80 (м, IH), 2.00-2.21 (м, 4H), 2.55-2.57 (м, 4H), 2.71 (с, ЗН), 3.18-3.32 (м, IH), 3.83 (с, ЗН), 3.92-4.05 (м, 2H), 4.10-4.20 (м, IH), 4.75-4.85 (м, IH), 6.79-6.91 (м, 2H), 7.06-7.16 (м, ЗН), 7.18-7.29 (м, ЗН). 2-Methoxy-ll-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 521): Yield 40%. 1 H NMR (400 MHz, CDCl 3 ): 1.73-1.80 (m, IH), 2.00-2.21 (m, 4H), 2.55-2.57 (m, 4H), 2.71 (s, 3H), 3.18-3.32 (m , IH), 3.83 (s, 3Н), 3.92-4.05 (m, 2H), 4.10-4.20 (m, IH), 4.75-4.85 (m, IH), 6.79-6.91 (m, 2H), 7.06-7.16 (m, ZN), 7.18-7.29 (m, ZN).
2-Фтop-ll-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 522): Выход 35%. 1H NMR (400 МГц, CDCl3): 1.40-1.47 (м, IH), 1.68-1.74 (м, IH), 1.80-2.14 (м, 4H), 2.44 (с, ЗН), 2.58-2.72 (м, 2H), 2.80-2-Ftop-ll-methyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 522): Yield 35%. 1 H NMR (400 MHz, CDCl 3 ): 1.40-1.47 (m, IH), 1.68-1.74 (m, IH), 1.80-2.14 (m, 4H), 2.44 (s, 3H), 2.58-2.72 (m , 2H), 2.80-
2.95 (м, 2H), 3.20-3.30 (м, 2H), 3.35-3.45 (м, IH), 3.49 (уш. с, IH), 6.70-6.81 (м, 2H), 6.80-2.95 (m, 2H), 3.20-3.30 (m, 2H), 3.35-3.45 (m, IH), 3.49 (br s, IH), 6.70-6.81 (m, 2H), 6.80-
6.96 (м, 2H), 7.12-7.23 (м, ЗН), 7.23-7.31 (м, 2H). 6.96 (m, 2H), 7.12-7.23 (m, ZN), 7.23-7.31 (m, 2H).
2-Изoпpoпил-ll-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 796): Выход 15%. 1H NMR (400 МГц, CDCl3): 1.29 (с, ЗН), 1.31 (с, ЗН), 1.35-1.41 (м, IH), 1.68 (м, IH), 2.09 (т, J = 7.6 Гц, 2H), 2.16 (с, ЗН), 2.57-2.77 (м, 7H), 3.00 (септ. J = 6.8 Гц, 2H), 4.00 (кв. J = 6.8 Гц, IH), 4.00-4.10 (м, IH), 4.70-4.80 (м, IH), 7.08-7.33 (м, 8H). 2-Isopropyl-ll-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 796): Yield 15%. 1 H NMR (400 MHz, CDCl 3 ): 1.29 (s, 3H), 1.31 (s, 3H), 1.35-1.41 (m, IH), 1.68 (m, IH), 2.09 (t, J = 7.6 Hz, 2H), 2.16 (s, 3H), 2.57-2.77 (m, 7H), 3.00 (sept. J = 6.8 Hz, 2H), 4.00 (q. J = 6.8 Hz, IH), 4.00-4.10 (m, IH ), 4.70-4.80 (m, IH), 7.08-7.33 (m, 8H).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 2,4-Дифтop-ll-мeтил-5-(3-фeнилпpoпил)-5,£,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 797): Выход 15%. 1H NMR (400 МГц, CDCl3): 1.36-1.68 (м, 2H), 1.78-2.10 (м, 4H), 2.37 (с, 1.5H), 2.40 (с, 1.5H), 2.61-2.81 (м, 4H), 3.05-3.19 (м, 2H), 3.36-3.42 (м, IH), 4.02-4.21 (м, IH), 6.59-6.96 (м, 3H), 7.13-7.20 (м, 3H), 7.25-7.30 (м, IH). SUBSTITUTE SHEET (RULE 26) 2,4-Difter-ll-methyl-5- (3-phenyl-propyl) -5, £, 7,8,9,10-hexahydro-7,10-epiminocyclogen [6] indole (compound 797): Yield 15%. 1 H NMR (400 MHz, CDCl 3 ): 1.36-1.68 (m, 2H), 1.78-2.10 (m, 4H), 2.37 (s, 1.5H), 2.40 (s, 1.5H), 2.61-2.81 (m , 4H), 3.05-3.19 (m, 2H), 3.36-3.42 (m, IH), 4.02-4.21 (m, IH), 6.59-6.96 (m, 3H), 7.13-7.20 (m, 3H), 7.25 -7.30 (m, IH).
l-Xлop-4,ll-димeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoreптa[ά] индол (соединение 798): Выход 18%. 1H NMR (400 МГц, CDCl3): 1.47-1.57 (м, IH), 1.85-1.95 (м, IH), 2.00-2.09 (м, 2H), 2.22-2.33 (м, 2H), 2.37 (с, 3H), 2.44 (с, 3H), 2.59-2.66 (м, 2H), 3.05-3.20 (м, IH), 3.60-3.67 (м, IH), 3.92-4.06 (м, 2H), 4.20-4.30 (м, IH), 6.90-6.98 (м, IH), 7.10-7.15 (м, 3H), 7.17-7.24 (м, IH), 7.26-7.32 (м, 2H). l-Chlorop-4, ll-dimethyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclorepta [ά] indole (compound 798): Yield 18%. 1 H NMR (400 MHz, CDCl 3 ): 1.47-1.57 (m, IH), 1.85-1.95 (m, IH), 2.00-2.09 (m, 2H), 2.22-2.33 (m, 2H), 2.37 (s , 3H), 2.44 (s, 3H), 2.59-2.66 (m, 2H), 3.05-3.20 (m, IH), 3.60-3.67 (m, IH), 3.92-4.06 (m, 2H), 4.20-4.30 (m, IH), 6.90-6.98 (m, IH), 7.10-7.15 (m, 3H), 7.17-7.24 (m, IH), 7.26-7.32 (m, 2H).
4-Фтop-l,ll-димeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол (соединение 199): Выход 15%. 1H NMR (400 МГц, CDCl3): 1.41-1.47 (м, IH), 1.65-1.71 (м, IH), 1.83-2.05 (м, 4H), 2.18 (с, 3H), 2.38 (с, 3H), 2.62-2.86 (м, 4H), 3.14-3.30 (м, 2H), 3.37-3.49 (м, 2H), 6.68-4.80 (м, 2H), 6.82-6.92 (м, IH), 7.13-7.21 (м, 3H), 7.25-7.30 (м, IH). 4-Ftop-l, ll-dimethyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole (compound 199): Yield 15% . 1 H NMR (400 MHz, CDCl 3 ): 1.41-1.47 (m, IH), 1.65-1.71 (m, IH), 1.83-2.05 (m, 4H), 2.18 (s, 3H), 2.38 (s, 3H ), 2.62-2.86 (m, 4H), 3.14-3.30 (m, 2H), 3.37-3.49 (m, 2H), 6.68-4.80 (m, 2H), 6.82-6.92 (m, IH), 7.13-7.21 (m, 3H), 7.25-7.30 (m, IH).
ll-Meтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ά] индол (соединение 519): Выход 37%. 1H NMR (400 МГц, CDCl3): 1.46-1.55 (м, IH), 1.88-1.92 (м, IH), 2.03-2.10 (м, 2H), 2.22-2.31 (м, 3H), 2.35 (с, 3H), 2.63- 2.67 (м, 2H), 3.05-3.15 (м, IH), 3.55-3.65 (м, IH), 3.94-4.08 (м, 2H), 4.18-4.26 (м, IH), 7.04- 7.18 (м, 4H), 7.19-7.22 (м, 2H), 7.26-7.30 (м, 2H), 7.40-7.50 (м, IH). ll-Methyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ά] indole (compound 519): Yield 37%. 1 H NMR (400 MHz, CDCl 3 ): 1.46-1.55 (m, IH), 1.88-1.92 (m, IH), 2.03-2.10 (m, 2H), 2.22-2.31 (m, 3H), 2.35 (s , 3H), 2.63- 2.67 (m, 2H), 3.05-3.15 (m, IH), 3.55-3.65 (m, IH), 3.94-4.08 (m, 2H), 4.18-4.26 (m, IH), 7.04 - 7.18 (m, 4H), 7.19-7.22 (m, 2H), 7.26-7.30 (m, 2H), 7.40-7.50 (m, IH).
2,4,ll-Tpимeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 8J)O): Выход 20%. 1H NMR (400 МГц, CDCl3): 1.27-1.36 (м, IH), 1.51-1.62 (м, 2H), 1.91-2.02 (м, 4H), 2.37 (с, 3H), 2.45 (с, 3H), 2.53 (с, 3H), 2.65-2.69 (м, 2H), 3.00-3.10 (м, IH), 3.8 (уш.с, IH), 4.03-4.21 (м, 2H), 4.4 (уш. с, IH), 6.70 (уш. с, IH), 7.07 (уш. с, IH), 7.10-7.18 (м, 2H), 7.20-7.24 (м, IH), 7.27-7.32 (м, 2H). 2,4, ll-Trimethyl-5- (3-phenyl-propyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepta [6] indole (compound 8J) O): Yield 20%. 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.36 (m, IH), 1.51-1.62 (m, 2H), 1.91-2.02 (m, 4H), 2.37 (s, 3H), 2.45 (s, 3H ), 2.53 (s, 3H), 2.65-2.69 (m, 2H), 3.00-3.10 (m, IH), 3.8 (br.s, IH), 4.03-4.21 (m, 2H), 4.4 (br.s , IH), 6.70 (br.s, IH), 7.07 (br.s, IH), 7.10-7.18 (m, 2H), 7.20-7.24 (m, IH), 7.27-7.32 (m, 2H).
2-Этил-ll-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 801): 2-Ethyl-ll-methyl-5- (3-phenyl-propyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclogene [6] indole (compound 801):
Выход 21%. 1H NMR (400 МГц, CDCl3): 1,29 (т, J = 7.6 Гц, 3H), 1.47-1.55 (м, IH), 1.89-1.93 (м, IH), 2.02-2.10 (м, 2H), 2.25-2.30 (м, 3H), 2.36 (с, 3H), 2.60-2.70 (м, 2H), 2.74 (кв, J = 7.6 Гц), 3.05-3.16 (м, IH), 3.6 (уш.с, IH), 3.91-4.06 (м, 2H), 4.18-4.24 (м, IH), 6.95-7.01 (м, IH), 7.11-7.23 (м, 4H), 7.20-7.34 (м, 3H). Yield 21%. 1 H NMR (400 MHz, CDCl 3 ): 1.29 (t, J = 7.6 Hz, 3H), 1.47-1.55 (m, IH), 1.89-1.93 (m, IH), 2.02-2.10 (m, 2H ), 2.25-2.30 (m, 3H), 2.36 (s, 3H), 2.60-2.70 (m, 2H), 2.74 (q, J = 7.6 Hz), 3.05-3.16 (m, IH), 3.6 (br. s, IH), 3.91-4.06 (m, 2H), 4.18-4.24 (m, IH), 6.95-7.01 (m, IH), 7.11-7.23 (m, 4H), 7.20-7.34 (m, 3H).
ll-Циклoгeкcил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 802): ll-Cyclohexyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogene [6] indole (compound 802):
Выход 20%, ЯМР 1H (CDCl3, δ, м.д.): 0.97-1.37 (м, 3H), 1.48-1.76 (м, 4H), 1.80-2.17 (м, 5H), 2.14 (т, 3J- 7.6 Гц, 2H), 2.38 (д, 2J= 16.8 Гц, IH), 2.42-2:53 (м, 2H), 2.69 (т, 3J= 7.6 Гц, 2H), Yield 20%, 1 H NMR (CDCl 3, δ, ppm): 0.97-1.37 (m, 3H), 1.48-1.76 (m, 4H), 1.80-2.17 (m, 5H), 2.14 (t, 3 J- 7.6 Hz, 2H), 2.38 (d, 2 J = 16.8 Hz, IH), 2.42-2: 53 (m, 2H), 2.69 (t, 3 J = 7.6 Hz, 2H),
78 78
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 2.70-2.79 (м, IH), 3.17 (дд, 2J = 16.8, 3J = 3.9 Гц, IH), 4.00-4.13 (м, 2H), 4.13-4.22 (м, IH), 4.80 (д, 3J= 3.9 Гц, IH), 7.11-7.18 (м, IH), 7.18-7.37 (м, 7H), 7.52 (д, 3J= 7.8 Гц, IH). SUBSTITUTE SHEET (RULE 26) 2.70-2.79 (m, IH), 3.17 (dd, 2 J = 16.8, 3 J = 3.9 Hz, IH), 4.00-4.13 (m, 2H), 4.13-4.22 (m, IH), 4.80 (d, 3 J = 3.9 Hz, IH), 7.11-7.18 (m, IH), 7.18-7.37 (m, 7H), 7.52 (d, 3 J = 7.8 Hz, IH).
ll-Бeнзил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол (соединение 803): Выход 10%, ЯМР 1H (CDCl3, δ, м.д.): 1.69-1.78 (м, IH), 2.08-2.17 (м, IH), 2.24-2.36 (м, 2H), 2.41-2.56 (м, 2H), 2.45 (д, 2J= 16.3 Гц, IH), 2.82-2.92 (м, 2H), 3.34 (дд, 2J = 16.3, 3J = 4.0 Гц, IH), 3.84 (д, 2J = 13.1 Гц, IH), 3.89- 3.91 (м, IH), 3.90 (д, 2J = 13.1 Гц, IH), 4.14-4.30 (м, 2H), 4.47 (д, 3J= 4.0 Гц, IH), 7.26-7.33 (м, IH), 7.33-7.56 (м, 12H), 7.65 (д, 3J= 7.6 Гц, IH). ll-Benzyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogept [ό] indole (compound 803): Yield 10%, 1 H NMR (CDCl 3 , δ, ppm): 1.69-1.78 (m, IH), 2.08-2.17 (m, IH), 2.24-2.36 (m, 2H), 2.41-2.56 (m, 2H), 2.45 (d, 2 J = 16.3 Hz, IH), 2.82-2.92 (m, 2H), 3.34 (dd, 2 J = 16.3, 3 J = 4.0 Hz, IH), 3.84 (d, 2 J = 13.1 Hz, IH), 3.89- 3.91 (m, IH), 3.90 (d, 2 J = 13.1 Hz, IH), 4.14-4.30 (m, 2H), 4.47 (d, 3 J = 4.0 Hz, IH), 7.26-7.33 (m, IH) 7.33-7.56 (m, 12H); 7.65 (d, 3 J = 7.6 Hz, IH).
2,1 l-Димeтил-5-(3-фeнилпpoпил)-6,7,8,9,10,l l-гeкcaгидpo-7,11- эпиминoциклooктa[/>] индол (соединение 520): Выход 57%, ЯМР 1H (CDCl3, δ, м.д.): 1.28-1.40 (м, IH, CH2), 1.47 (уш.д, 2J= 13.2 Гц, IH, CH2), 1.72 (уш.д, 2J= 11.9 Гц, IH, CH2), 1.84 (уш.д, 2J = 11.9 Гц, IH, CH2), 2.12-2.25 (м, 4H, CH2), 2.41 (д, 2J = 17.1 Гц, IH, CH2), 2.47 (с, ЗН, CH3), 2.58 (с, ЗН, CH3), 2.76 (т, 3J= 7.6 Гц, 2H, CH2), 3.16 (дд, 2J= 17.1, 3J= 6.8 Гц, IH, CH2), 3.38-3.46 (м, IH, CHN), 4.15 (т, 3J = 7.6 Гц, 2H, CH2), 4.30 ( уш.с, IH, CH), 7.10 (дд, 2J = 17.1, 4J = 1.3 Гц, Ш, CH), 7.27 (уш.д, 3J = 7.8 Гц, IH, CH), 7.30-7.43 (м, 6H, CH). 2.1 l-Dimethyl-5- (3-phenylpropyl) -6,7,8,9,10, l l-hexahydro-7,11-epiminocyclooct [/>] indole (compound 520): Yield 57%, NMR 1 H (CDCl 3, δ, ppm): 1.28-1.40 (m, IH, CH 2 ), 1.47 (brd, 2 J = 13.2 Hz, IH, CH 2 ), 1.72 (brd, 2 J = 11.9 Hz, IH, CH 2 ), 1.84 (broad d, 2 J = 11.9 Hz, IH, CH 2 ), 2.12-2.25 (m, 4H, CH 2 ), 2.41 (d, 2 J = 17.1 Hz, IH, CH 2 ), 2.47 (s, 3H, CH 3 ), 2.58 (s, 3H, CH 3 ), 2.76 (t, 3 J = 7.6 Hz, 2H, CH 2 ), 3.16 (dd, 2 J = 17.1, 3 J = 6.8 Hz, IH, CH 2 ), 3.38-3.46 (m, IH, CHN), 4.15 (t, 3 J = 7.6 Hz, 2H, CH 2 ), 4.30 (br.s, IH, CH), 7.10 (dd, 2 J = 17.1, 4 J = 1.3 Hz, W, CH), 7.27 (br.s, 3 J = 7.8 Hz, IH, CH), 7.30-7.43 (m, 6H, CH) .
2,3»8-Tpимeтил-5-(3-фeни лпpoпил)-2,3i4,5-тeтpaгидpo- liУ-пиридо [4,3-^] индол 2,3 ” 8-Trimethyl-5- (3-phenyl lpropyl) -2,3i4,5-tetrahydroli-pyrido [4,3- ^] indole
(соединение 484): Выход 35%. 1H ЯМР (400 МГц, CDCl3) δ 1.24 (д, ЗН, J=6.3 Гц), 2.09 (м, IH), 2.48 (с, ЗН), 2.52 (с, ЗН), 2.53 (дд, IH), 2.47 (с, ЗН), 2.68 (т, 2H, J=7.3 Гц), 2.82 (дд, IH, J=4.3, 16.1 Гц), 2.93 (м, IH), 3.70 (д, IH, J=14.4 Гц), 3.92 (д, IH, J=14.4 Гц), 4.04 (т, 2H), 7.34 - 6.98 (м, 8H). (Compound 484): Yield 35%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.24 (d, 3H, J = 6.3 Hz), 2.09 (m, IH), 2.48 (s, 3H), 2.52 (s, 3H), 2.53 (dd, IH) , 2.47 (s, 3Н), 2.68 (t, 2H, J = 7.3 Hz), 2.82 (dd, IH, J = 4.3, 16.1 Hz), 2.93 (m, IH), 3.70 (d, IH, J = 14.4 Hz), 3.92 (d, IH, J = 14.4 Hz), 4.04 (t, 2H), 7.34 - 6.98 (m, 8H).
Алкилирование 2-фeнoкcиэтилxлopидoм  Alkylation with 2-phenoxyethylchloride
К раствору 1 ммоль индола, в 10 мл DMF добавляют 3 ммоль NaH при 00C. Смесь выдерживают 30 мин при этой температуре, а затем быстро прибавляют раствор 2 ммоль феноксиэтwιхлорида в 10 мл DMF и каталитические количества NaI. Смесь перемешивают 12 часов при комнатной температуре. Реакционную смесь разлагают водой. Экстрагируют этилацетатом (3*30 мл), сушат над поташом и упаривают в вакууме. Продукт очищают методом колоночной хроматографии (дихлорметан-метанол-аммиак 100-10-1). После очистки продукт растворяют в метаноле, пропускают HCl (газ) и упаривают в вакууме. To a solution of 1 mmol of indole in 10 ml of DMF was added 3 mmol of NaH at 0 ° C. The mixture was held at this temperature for 30 minutes, and then a solution of 2 mmol of phenoxyethyl chloride in 10 ml of DMF and catalytic amounts of NaI were quickly added. The mixture was stirred for 12 hours at room temperature. The reaction mixture is decomposed with water. Extracted with ethyl acetate (3 * 30 ml), dried over potash and evaporated in vacuo. The product is purified by column chromatography (dichloromethane-methanol-ammonia 100-10-1). After purification, the product is dissolved in methanol, HCl (gas) is passed and evaporated in vacuo.
2-Meтoкcи-ll-мeтил-5-(2-фeнилэтoкcи)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол (соединение 804): Выход 33%. H NMR (400 МГц, CDCl3): 1.48-1.55 (м, IH), 1.90 (т, J = 9.6 Гц, IH), 2.26-2.33 (м, 2H), 2.37 (с, ЗН), 2.44 (д, J = 16.4 Гц, IH), 3.24-3.29 (м, IH), 3.62-3.70 (м, IH), 3.85 (с, ЗН), 4.16-4.22 (м, ЗН), 4.30-4.42 (м, 2H), 6.70-6.80 (м, 2H), 7.10 (дд, J = 2.5, 6.3 Гц, IH), 6.85-6.95 (м, 2H), 7.15-7.25 (м, ЗН). 2-Methoxy-ll-methyl-5- (2-phenylethoxy) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepto [/>] indole (compound 804): Yield 33%. H NMR (400 MHz, CDCl 3 ): 1.48-1.55 (m, IH), 1.90 (t, J = 9.6 Hz, IH), 2.26-2.33 (m, 2H), 2.37 (s, 3H), 2.44 (d , J = 16.4 Hz, IH), 3.24-3.29 (m, IH), 3.62-3.70 (m, IH), 3.85 (s, ZN), 4.16-4.22 (m, ZN), 4.30-4.42 (m, 2H ), 6.70-6.80 (m, 2H), 7.10 (dd, J = 2.5, 6.3 Hz, IH), 6.85-6.95 (m, 2H), 7.15-7.25 (m, 3H).
79 79
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 2-Фтop-ll-мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9,10-гeкca'гидpo-7,10- эпиминoциклoгeптa[/>] индол (соединение 805): Выход 71%. 1H NMR (400 МГц, CDCl3): 1.52-1.57 (м, IH), 1.91 (т, J = 9.1 Гц, IH), 2.30-2.38 (м, 2H), 2.41 (с, 3H), 2.52 (д, J - 16.4 Гц, IH), 3.27-3.33 (м, IH), 3.69-3.76 (м, IH), 4.20 (т, J = 5.6 Гц, 2H), 4.22 (д, J = 4.6 Гц, IH), 4.32-4.44 (м, 2H), 6.70-6.78 (м, 2H), 6.87-6.93 (м, 2H), 7.10 (дд, J = 2.5, 7.1 Гц, IH), 7.18-7.24 (м, 3H). SUBSTITUTE SHEET (RULE 26) 2-Ftop-ll-methyl-5- (2-phenoxyethyl) -5,6,7,8,9,10-hexa'hydro-7,10-epiminocyclohepta [/>] indole (compound 805): 71% yield . 1 H NMR (400 MHz, CDCl 3 ): 1.52-1.57 (m, IH), 1.91 (t, J = 9.1 Hz, IH), 2.30-2.38 (m, 2H), 2.41 (s, 3H), 2.52 ( d, J - 16.4 Hz, IH), 3.27-3.33 (m, IH), 3.69-3.76 (m, IH), 4.20 (t, J = 5.6 Hz, 2H), 4.22 (d, J = 4.6 Hz, IH ), 4.32-4.44 (m, 2H), 6.70-6.78 (m, 2H), 6.87-6.93 (m, 2H), 7.10 (dd, J = 2.5, 7.1 Hz, IH), 7.18-7.24 (m, 3H )
2,3,8-Tpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-6]индoл  2,3,8-Trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4.3-6] indole
(соединение 806): Выход 36%. 1H ЯМР (400 МГц, CDCl3) δ 1.27 (д, ЗН, J=6.3 Гц), 2.47 (с, 3H), 2.52 (с, ЗН), 2.68 (м, IH), 3.00 (м, 2H), 3 Jl (д, IH, J=HA Гц), 3.91 (д, IH, J=14.4 Гц), 4.19 (т, 2H, J=5.9 Гц), 4.42 (т, 2H, J=5.9 Гц), 6.82 (д, 2H, J-8.1 Гц), 6.95 (т, IH, J=7.3 Гц), 7.02 (д, IH, J=8.6 Гц), 7.25 (м, 4H). (compound 806): Yield 36%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.27 (d, 3H, J = 6.3 Hz), 2.47 (s, 3H), 2.52 (s, 3H), 2.68 (m, IH), 3.00 (m, 2H) , 3 Jl (d, IH, J = HA Hz), 3.91 (d, IH, J = 14.4 Hz), 4.19 (t, 2H, J = 5.9 Hz), 4.42 (t, 2H, J = 5.9 Hz), 6.82 (d, 2H, J-8.1 Hz), 6.95 (t, IH, J = 7.3 Hz), 7.02 (d, IH, J = 8.6 Hz), 7.25 (m, 4H).
2-Meтил-ll-мeтил-5-(2-фeнилэтoкcи)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [Z>] индол (соединение 807): Выход 33%, спектр 1H ЯМР (400 МГц, CDCl3): 1.61-1.64 (м, IH), 1.97-2.02 (м, IH), 2.38-2.45 (м, 2H), 2.48 (с, 6H, CH3-N, CH3-Ar), 2.59 (д, J = 5.2 Гц, IH), 3.35 (дд, J = 16.5 Гц, J = 4.5 Гц, IH), 3.79-3.82 (м, IH), 4.23 (т, J = 4.5 Гц, 2H, CH2-O), 4.38-4.46 (м, ЗН), 6.76-6.78 (м, 2H), 6.91-6.95 (м, IH), 7.03-7.05 (м, IH), 7.22-7.25 (м, 2H), 7.28-7.31 (м, 2H). 2-Methyl-ll-methyl-5- (2-phenylethoxy) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [Z>] indole (compound 807): Yield 33%, spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.61-1.64 (m, IH), 1.97-2.02 (m, IH), 2.38-2.45 (m, 2H), 2.48 (s, 6H, CH 3 -N, CH 3 -Ar), 2.59 (d, J = 5.2 Hz, IH), 3.35 (dd, J = 16.5 Hz, J = 4.5 Hz, IH), 3.79-3.82 (m, IH), 4.23 (t, J = 4.5 Hz, 2H, CH 2 -O), 4.38-4.46 (m, 3H), 6.76-6.78 (m, 2H), 6.91-6.95 (m, IH), 7.03-7.05 (m, IH), 7.22-7.25 ( m, 2H), 7.28-7.31 (m, 2H).
ll-Meтил-5-(2-фeнилэтoкcи)-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[6]индoл (соединение 808): Выход 75%, спектр 1H ЯМР (400 МГц, CDCl3): 1.51-1.61 (м, IH), 1.95- 1.99 (м, IH), 2.36-2.42 (м, 2H), 2.46 (с, ЗН, CH3-N), 2.56 (д, J = 5.2 Гц, IH), 3.35 (дд, J = 16.6 Гц, J = 4.5 Гц, IH), 3.74-3.78 (м, IH), 4.24 (т, J = 5.5 Гц, 2H, CH2-O), 4.36 (д, J = 4.8 Гц, IH), 4.41-4.48 (м, 2H), 6.76-6.78 (м, 2H), 6.91-6.94 (м, IH), 7.11-7.14 (м, IH), 7.17-7.26 (м, ЗН) 7.35 (д, J = 7.5 Гц, IH), 7.49 (д, J = 7.5 Гц, IH). ll-Methyl-5- (2-phenylethoxy) -5,6,7,8,9,10-hexahydro-7,10-epiminocycloheptol [6] indole (compound 808): Yield 75%, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.51-1.61 (m, IH), 1.95-1.99 (m, IH), 2.36-2.42 (m, 2H), 2.46 (s, 3H, CH 3 -N), 2.56 (d, J = 5.2 Hz, IH), 3.35 (dd, J = 16.6 Hz, J = 4.5 Hz, IH), 3.74-3.78 (m, IH), 4.24 (t, J = 5.5 Hz, 2H, CH 2 -O), 4.36 (d, J = 4.8 Hz, IH), 4.41-4.48 (m, 2H), 6.76-6.78 (m, 2H), 6.91-6.94 (m, IH), 7.11-7.14 (m, IH), 7.17- 7.26 (m, ZN) 7.35 (d, J = 7.5 Hz, IH), 7.49 (d, J = 7.5 Hz, IH).
Алкилирование 2-apилэтилтoзилaтaми или бромидами  Alkylation with 2-apylethyltosylates or bromides
К раствору 1 ммоль индола в 5 мл ДМФА добавляют 120 мг (4 ммоль) NaH при O0C. Смесь выдерживают 30 мин при этой температуре, а затем быстро прибавляют раствор 3 ммоль тозилата или бромида в 5 мл ДМФА. Смесь перемешивают 12 часов при комнатной температуре. Реакционную смесь разлагают водой. Экстрагируют этилацетатом (3*50 мл), сушат над поташом и упаривают в вакууме. Продукт очищают методом колоночной хроматографии (дихлорметан-метанол 4-1). После очистки продукт растворяют в метаноле, пропускают HCl (газ.) и упаривают в вакууме. To a solution of 1 mmol of indole in 5 ml of DMF was added 120 mg (4 mmol) of NaH at O 0 C. The mixture was held for 30 minutes at this temperature, and then a solution of 3 mmol of tosylate or bromide in 5 ml of DMF was quickly added. The mixture was stirred for 12 hours at room temperature. The reaction mixture is decomposed with water. Extracted with ethyl acetate (3 * 50 ml), dried over potash and evaporated in vacuo. The product is purified by column chromatography (dichloromethane-methanol 4-1). After purification, the product is dissolved in methanol, HCl (gas) is passed through and evaporated in vacuo.
2-Meтoкcи-ll-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [A] индол (соединение 113): Выход 60%. 1H NMR (400 МГц, CDCl3): 1.26-1.32 (м, IH), 1.80-1.88 (м, 2H), 2.27 (с, ЗН), 2.15-2.31 (м, 2H), 2.58-2.66 (м, IH), 2.96- 2-Methoxy-ll-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [A] indole (compound 113): Yield 60%. 1 H NMR (400 MHz, CDCl 3 ): 1.26-1.32 (m, IH), 1.80-1.88 (m, 2H), 2.27 (s, 3H), 2.15-2.31 (m, 2H), 2.58-2.66 (m , IH), 2.96-
80 80
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 3.08 (м, 2H), 3.47-3.53 (м, IH), 3.86 (с, 3H), 4.17 (т, J = 6.7 Гц, 2H), 4.22 (д, J = 5.4 Гц, IH), 6.83 (дд, J = 2.6, 6.2 Гц, IH), 6.86-6.95 (м, 3H), 7.15-7.24 (м, 3H), 7.23 (д, J = 8.8 Гц, IH). 2-Meтoкcи-5-[2-(4-Meтoкcифeнил)этил]-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 430): Выход 47%. 1H NMR (400 МГц, CDCl3): 1.30-1.38 (м, IH), 1.88-1.93 (м, 2H), 2,24-2,31 (м, IH), 2.34 (с, 3H), 2.37-2.45 (м, IH), 2.62- 2.67 (м, IH), 2.91-3.02 (м, 2H), 3.61-3.64 (м, IH), 3.72 (с, 3H), 3.86 (с, 3H), 4.14 (т, J = 6.6 Гц, 2H), 4.35 (д, J = 5.3 Гц, IH), 6.72 (д, J = 8.8 Гц, 2H), 6.78 (д, J = 8.8 Гц, 2H), 8.85 (дд, J = 2.5, 6.3 Гц, IH), 6.91 (д, J = 2.5 Гц, IH), 7.24 (д, J = 8.9 Гц, IH). SUBSTITUTE SHEET (RULE 26) 3.08 (m, 2H), 3.47-3.53 (m, IH), 3.86 (s, 3H), 4.17 (t, J = 6.7 Hz, 2H), 4.22 (d, J = 5.4 Hz, IH), 6.83 (dd , J = 2.6, 6.2 Hz, IH), 6.86-6.95 (m, 3H), 7.15-7.24 (m, 3H), 7.23 (d, J = 8.8 Hz, IH). 2-Methoxy-5- [2- (4-Methoxyphenyl) ethyl] -ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 430): Yield 47% 1 H NMR (400 MHz, CDCl 3 ): 1.30-1.38 (m, IH), 1.88-1.93 (m, 2H), 2.24-2.31 (m, IH), 2.34 (s, 3H), 2.37 -2.45 (m, IH), 2.62- 2.67 (m, IH), 2.91-3.02 (m, 2H), 3.61-3.64 (m, IH), 3.72 (s, 3H), 3.86 (s, 3H), 4.14 (t, J = 6.6 Hz, 2H), 4.35 (d, J = 5.3 Hz, IH), 6.72 (d, J = 8.8 Hz, 2H), 6.78 (d, J = 8.8 Hz, 2H), 8.85 (dd , J = 2.5, 6.3 Hz, IH), 6.91 (d, J = 2.5 Hz, IH), 7.24 (d, J = 8.9 Hz, IH).
2-Meтoкcи-ll-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 167): Выход 57%. 1H NMR (400 МГц, CDCl3): 1.28-1.34 (м, IH), 1.86-1.91 (м, 2H), 2,21-2,31 (м, IH), 2.27 (с, 3H), 2.31 (с, 3H), 2.33-2.43 (м, IH), 2.60-2.69 (м, IH), 2.92-3.03 (м, 2H), 3.56-3.64 (м, IH), 3.86 (с, 3H), 4.15 (т, J = 6.5 Гц, 2H), 4.35 (д, J = 5.3 Гц, IH), 6.78 (д, J = 7.8 Гц, 2H), 8.85 (дд, J = 2.5, 6.3 Гц, IH), 6.91 (д, J = 2.5 Гц, IH), 7.00 (д, J = 8.8 Гц, 2H), 7.24 (д, J = 8.9 Гц, IH). 2-Methoxy-ll-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 167): Yield 57% 1 H NMR (400 MHz, CDCl 3 ): 1.28-1.34 (m, IH), 1.86-1.91 (m, 2H), 2.21-2.31 (m, IH), 2.27 (s, 3H), 2.31 (s, 3H), 2.33-2.43 (m, IH), 2.60-2.69 (m, IH), 2.92-3.03 (m, 2H), 3.56-3.64 (m, IH), 3.86 (s, 3H), 4.15 (t, J = 6.5 Hz, 2H), 4.35 (d, J = 5.3 Hz, IH), 6.78 (d, J = 7.8 Hz, 2H), 8.85 (dd, J = 2.5, 6.3 Hz, IH), 6.91 (d, J = 2.5 Hz, IH), 7.00 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.9 Hz, IH).
5-[2-(4-Xлopфeнил)этил]-2-мeтoкcи-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол (соединение 378): Выход 26%. 1H NMR (400 МГц, CDCl3): 1.27-1.34 (м, IH), 1.79-1.88 (м, 2H), 2,18-2,33 (м, 2H), 2.27 (с, 3H), 2.60-2.70 (м, IH), 2.92- 3.03 (м, 2H), 3.49-3.56 (м, IH), 3.86 (с, 3H), 4.15 (т, J = 6.8 Гц, 2H), 4.35 (д, J = 5.1 Гц, IH), 6.80 (д, J = 8.6 Гц, 2H), 8.83 (дд, J = 2.3, 6.5 Гц, IH), 6.91 (д, J - 2.3 Гц, IH), 7.15 (д, J = 8.6 Гц, 2H), 7.21 (д, J = 8.8 Гц, IH). 5- [2- (4-Chlorophenyl) ethyl] -2-methoxy-ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole (compound 378): Yield 26%. 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.34 (m, IH), 1.79-1.88 (m, 2H), 2.18-2.33 (m, 2H), 2.27 (s, 3H), 2.60 -2.70 (m, IH), 2.92-3.03 (m, 2H), 3.49-3.56 (m, IH), 3.86 (s, 3H), 4.15 (t, J = 6.8 Hz, 2H), 4.35 (d, J = 5.1 Hz, IH), 6.80 (d, J = 8.6 Hz, 2H), 8.83 (dd, J = 2.3, 6.5 Hz, IH), 6.91 (d, J - 2.3 Hz, IH), 7.15 (d, J = 8.6 Hz, 2H), 7.21 (d, J = 8.8 Hz, IH).
2-Meтoкcи-ll-мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 219): Выход 67%. 1H NMR (400 МГц, CDCl3): 1.27-1.33 (м, IH), 1.74-1.84 (м, 2H), 2.10 (с, 3H), 2,14-2,26 (м, 2H), 2.24 (с, 3H), 2.58-2.68 (м, IH), 2.98-3.05 (м, 2H), 3.40-3.57 (м, IH), 3.86 (с, 3H), 4.12-4.20 (м, 3H), 6.81 (дд, J = 2.3, 6.6 Гц, IH), 6.91 (д, J = 2.3 Гц, IH), 7.00-7.15 (м, 3H), 7.22 (д, J = 8.8 Гц, IH). 2-Methoxy-ll-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 219): Yield 67% 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.33 (m, IH), 1.74-1.84 (m, 2H), 2.10 (s, 3H), 2.14-2.26 (m, 2H), 2.24 (s, 3H), 2.58-2.68 (m, IH), 2.98-3.05 (m, 2H), 3.40-3.57 (m, IH), 3.86 (s, 3H), 4.12-4.20 (m, 3H), 6.81 (dd, J = 2.3, 6.6 Hz, IH), 6.91 (d, J = 2.3 Hz, IH), 7.00-7.15 (m, 3H), 7.22 (d, J = 8.8 Hz, IH).
5-[2-(4-Фтopфeнил)этил]-2-Meтoкcи-ll-мeтил-5,6,7,8,*9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[£] индол (соединение 327): Выход 66%. 1H NMR (400 МГц, CDCl3): 1.27-1.34 (м, IH), 1.80-1.91 (м, 2H), 2,18-2,39 (м, 2H), 2.30 (с, 3H), 2.62-2.72 (м, IH), 2.95- 3.05 (м, 2H), 3.50-3.59 (м, IH), 3.86 (с, 3H), 4.15 (т, J = 6.8 Гц, 2H), 4.35 (д, J = 5.3 Гц, IH), 6.80-6.95 (м, 6H), 7.21 (д, J = 8.8 Гц, IH). 5- [2- (4-Fluorophenyl) ethyl] -2-Methoxy-ll-methyl-5,6,7,8, * 9,10-hexahydro-7,10-epiminocyclohept [£] indole (compound 327): Yield 66%. 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.34 (m, IH), 1.80-1.91 (m, 2H), 2.18-2.39 (m, 2H), 2.30 (s, 3H), 2.62 -2.72 (m, IH), 2.95-3.05 (m, 2H), 3.50-3.59 (m, IH), 3.86 (s, 3H), 4.15 (t, J = 6.8 Hz, 2H), 4.35 (d, J = 5.3 Hz, IH), 6.80-6.95 (m, 6H), 7.21 (d, J = 8.8 Hz, IH).
2-Фтop-ll-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 114): Выход 75%. 1H NMR (400 МГц, CDCl3): 1.22-1.32 (м, IH), 1.77-1.85 (м, 2H), 2.25 (с, 3H), 2.12-2.31 (м, 2H), 2.61-2.66 (м, IH), 2.96- 3.08 (м, 2H), 3.47-3.50 (м, IH), 4.16 (д, J = 5.3.Гц, IH), 4.19 (т, J = 6.6 Гц, 2H), 6.86-6.93 (м, 3H), 7.10 (дд, J = 2.5, 7.1 Гц, IH), 7.18-7.24 (м, 4H). 2-Ftop-ll-methyl-5- (2-phenylethyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepta [6] indole (compound 114): Yield 75%. 1 H NMR (400 MHz, CDCl 3 ): 1.22-1.32 (m, IH), 1.77-1.85 (m, 2H), 2.25 (s, 3H), 2.12-2.31 (m, 2H), 2.61-2.66 (m , IH), 2.96-3.08 (m, 2H), 3.47-3.50 (m, IH), 4.16 (d, J = 5.3.Hz, IH), 4.19 (t, J = 6.6 Hz, 2H), 6.86-6.93 (m, 3H), 7.10 (dd, J = 2.5, 7.1 Hz, IH), 7.18-7.24 (m, 4H).
81 81
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 2-Фтop-5-[2-(4-мeтoкcифeнил)этил]-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[£]индoл (соединение 431): Выход 47%. 1H NMR (400 МГц, CDCl3): 1.27-1.34 (м, IH), 1.77-1.80 (м, 2H), 2.12-2.30 (м, 2H), 2.23 (с, 3H), 2.64-2.72 (м, IH), 2.89- 3.01 (м, 2H), 3.42-3.48 (м, IH), 3.74 (с, 3H), 4.10 (д, J = 5.1 Гц, IH), 4.14 (т, J = 6.6 Гц, 2H), 6.73 (д, J = 8.8 Гц, 2H), 6.79 (д, J = 8.8 Гц, 2H), 6.86-6.91 (дт, J = 2.5, 6.6 Гц, IH), 7.10 (дд, J - 7.3, 2.5 Гц, IH), 7.16-7.25 (м, IH). SUBSTITUTE SHEET (RULE 26) 2-Ftop-5- [2- (4-methoxyphenyl) ethyl] -ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohept [£] indole (compound 431): Yield 47% 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.34 (m, IH), 1.77-1.80 (m, 2H), 2.12-2.30 (m, 2H), 2.23 (s, 3H), 2.64-2.72 (m , IH), 2.89- 3.01 (m, 2H), 3.42-3.48 (m, IH), 3.74 (s, 3H), 4.10 (d, J = 5.1 Hz, IH), 4.14 (t, J = 6.6 Hz, 2H), 6.73 (d, J = 8.8 Hz, 2H), 6.79 (d, J = 8.8 Hz, 2H), 6.86-6.91 (dt, J = 2.5, 6.6 Hz, IH), 7.10 (dd, J - 7.3 , 2.5 Hz, IH), 7.16-7.25 (m, IH).
2-Фтop-ll-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [Z)] индол (соединение 168): Выход 46%. 1H NMR (400 МГц, CDCl3): 1.27-1.30 (м, IH), 1.79-1.83 (м, 2H), 2.11-2.24 (м, 2H), 2.24 (с, 3H), 2.28 (с, 3H), 2.64-2.70 (м, IH), 2.91-3.03 (м, 2H), 3.45-3.52 (м, IH), 4.10-4.20 (м, 3H), 6.78 (д, J = 8.8 Гц, 2H), 6.86-6.91 (дт, J = 2.5, 6.6 Гц, IH), 7.00 (д, J = 7.8 Гц, 2H), 7.10 (дд, J = 7.1, 2.5 Гц, IH), 7.20-7.25 (м, IH). 2-Ftop-ll-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [Z)] indole (compound 168): The yield is 46%. 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.30 (m, IH), 1.79-1.83 (m, 2H), 2.11-2.24 (m, 2H), 2.24 (s, 3H), 2.28 (s, 3H ), 2.64-2.70 (m, IH), 2.91-3.03 (m, 2H), 3.45-3.52 (m, IH), 4.10-4.20 (m, 3H), 6.78 (d, J = 8.8 Hz, 2H), 6.86-6.91 (dt, J = 2.5, 6.6 Hz, IH), 7.00 (d, J = 7.8 Hz, 2H), 7.10 (dd, J = 7.1, 2.5 Hz, IH), 7.20-7.25 (m, IH) .
2-Фтop-ll-мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>]индoл (соединение 220): Выход 56%. 1H NMR (400 МГц, CDCl3): 1.27-1.30 (м, IH), 1.76-1.84 (м, 2H), 2.05 (с, 3H), 2.15-2.34 (м, 2H), 2.25 (с, 3H), 2.57-2.64 (м, IH), 3.03 (т, J = 6.6 Гц, 2H), 3.45-3.52 (м, IH), 4.16-4.20 (м, 3H), 6.78 (д, J = 7.3 Гц, 2H), 6.90 (дт, J = 2.5, 6.6 Гц, IH), 7.01-7.11 (м, 4H), 7.20г7.23 (м, IH). 2-Ftop-ll-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole (compound 220): The yield is 56%. 1 H NMR (400 MHz, CDCl 3 ): 1.27-1.30 (m, IH), 1.76-1.84 (m, 2H), 2.05 (s, 3H), 2.15-2.34 (m, 2H), 2.25 (s, 3H ), 2.57-2.64 (m, IH), 3.03 (t, J = 6.6 Hz, 2H), 3.45-3.52 (m, IH), 4.16-4.20 (m, 3H), 6.78 (d, J = 7.3 Hz, 2H), 6.90 (dt, J = 2.5, 6.6 Hz, IH), 7.01-7.11 (m, 4H), 7.20–7.23 (m, IH).
5-[2-(4-Xлopфeнил)этил]-2-фтop-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[£] индол (соединение 379): Выход 40%. 1H NMR (400 МГц, CDCl3): 1.23-1.28 (м, IH), 1.77-1.88 (м, 2H), 2.16 (с, 3H), 2.19-2.32 (м, 2H), 2.65-2.70 (м, IH), 2.94- 3.06 (м, 2H), 3.50-3.58 (м, IH), 4.15-4.20 (м, 3H), 6.78 (д, J = 8.3 Гц, 2H), 6.90 (дт, J = 2.3, 6.8 Гц, IH), 7.04-7.12 (м, 4H), 7.15 (д, J = 8.3 Гц, 2H), 7.16-7.23 (м, IH). 5- [2- (4-Chlorophenyl) ethyl] -2-fluorop-ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocycloheptide [£] indole (compound 379): Yield 40% 1 H NMR (400 MHz, CDCl 3 ): 1.23-1.28 (m, IH), 1.77-1.88 (m, 2H), 2.16 (s, 3H), 2.19-2.32 (m, 2H), 2.65-2.70 (m , IH), 2.94-3.06 (m, 2H), 3.50-3.58 (m, IH), 4.15-4.20 (m, 3H), 6.78 (d, J = 8.3 Hz, 2H), 6.90 (dt, J = 2.3 , 6.8 Hz, IH), 7.04-7.12 (m, 4H), 7.15 (d, J = 8.3 Hz, 2H), 7.16-7.23 (m, IH).
2-Фтop-5-[2-(4-фтopфeнил)этил]-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 328): Выход 70%. 1H NMR (400 МГц, DMSO- D6): 1.02-1.22 (м, 0.5H), 1.46-1.55 (м, IH), 1.89-2.07 (м, IH), 2.14-2.24 (м, 0.5 H), 2.27 (с, 0.5 H), 2.32-2.40 (м, IH), 2.44 (д, J = 5.1 Гц, 1.5H), 2.54 (с, 0.5 H), 2.77 (д, J = 5.1 Гц, 1.5H), 2.84-2.89 (м, 0.5H), 2.91-3.01 (м, 2H), 3.41-3.47 (м, 0.5H), 4.03-4.38 (м, 3H), 4,90-5.05 (м, IH), 6.92-7.10 (м, 5H), 7.28-7.55 (м, 2H), 10.5 (уш. с, 0.5H), 11.3 (уш. с, 0.5H). 2-Ftop-5- [2- (4-fluorophenyl) ethyl] -ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 328): Yield 70% 1 H NMR (400 MHz, DMSO-D 6 ): 1.02-1.22 (m, 0.5H), 1.46-1.55 (m, IH), 1.89-2.07 (m, IH), 2.14-2.24 (m, 0.5 H) , 2.27 (s, 0.5 H), 2.32-2.40 (m, IH), 2.44 (d, J = 5.1 Hz, 1.5H), 2.54 (s, 0.5 H), 2.77 (d, J = 5.1 Hz, 1.5H ), 2.84-2.89 (m, 0.5H), 2.91-3.01 (m, 2H), 3.41-3.47 (m, 0.5H), 4.03-4.38 (m, 3H), 4.90-5.05 (m, IH) 6.92-7.10 (m, 5H), 7.28-7.55 (m, 2H), 10.5 (br s, 0.5H), 11.3 (br s, 0.5H).
2-Изoпpoпил-ll-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [b] индол (соединение 809): Выход 66%. 1H NMR (400 МГц, CDCl3): 1.30-1.35 (м, IH), 1.32 (с, 3H), 1.33 (с, 3H), 1.83-1.92 (м, 2H), 2.18-2.26 (м, IH), 2.29 (с, 3H), 2,31-2,38 (м, IH), 2.60-2.67 (м, IH), 2.98-3.06 (м, 2H), 3.50-3.58 (м, IH), 4.14-4.22 (м, 2H), 4.30 (д, J = 5.2 Гц, IH), 6.90-7.00 (м, 2H), 7.02 (дд, J = 1.5, 7.2 Гц, IH), 7.19-7.23 (м, 3H), 7.24-7.34 (м, 2H). 2-Isopropyl-ll-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole (compound 809): Yield 66%. 1 H NMR (400 MHz, CDCl 3 ): 1.30-1.35 (m, IH), 1.32 (s, 3H), 1.33 (s, 3H), 1.83-1.92 (m, 2H), 2.18-2.26 (m, IH ), 2.29 (s, 3H), 2.31-2.38 (m, IH), 2.60-2.67 (m, IH), 2.98-3.06 (m, 2H), 3.50-3.58 (m, IH), 4.14 -4.22 (m, 2H), 4.30 (d, J = 5.2 Hz, IH), 6.90-7.00 (m, 2H), 7.02 (dd, J = 1.5, 7.2 Hz, IH), 7.19-7.23 (m, 3H ), 7.24-7.34 (m, 2H).
82 82
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) ll-мeтил-2-этил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[Z>] индол (соединение 810): Выход 59%. 1H NMR (400 МГц, CDCl3): 1.29 (т, J = 7.6 Гц, 3H), 1.87-2.20 (м, 3H), 2.26-2.52 (м, 2H), 2.40 (с, 3H), 2.55-2.65 (м, IH), 2.79 (кв, J = 7.6 Гц, 2H), 3.00-3.15 (м, 2H), 3.69-3.77 (м, IH), 4.15-4.30 (м, 2H), 4.42-4.54 (м, IH), 6.89-6.98 (м, 2H), 7.07-7.38 (м, 6H). SUBSTITUTE SHEET (RULE 26) ll-methyl-2-ethyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [Z>] indole (compound 810): Yield 59%. 1 H NMR (400 MHz, CDCl 3 ): 1.29 (t, J = 7.6 Hz, 3H), 1.87-2.20 (m, 3H), 2.26-2.52 (m, 2H), 2.40 (s, 3H), 2.55- 2.65 (m, IH), 2.79 (q, J = 7.6 Hz, 2H), 3.00-3.15 (m, 2H), 3.69-3.77 (m, IH), 4.15-4.30 (m, 2H), 4.42-4.54 ( m, IH), 6.89-6.98 (m, 2H), 7.07-7.38 (m, 6H).
2,ll-Димeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 112): Выход 72%. 1H NMR (400 МГц, CDCl3): 1.28-1.35 (м, IH), 1.83-1.95 (м, 2H), 2,20-2,39 (м, 2H), 2.32 (с, 3H), 2.46 (с, 3H), 2.60-2.70 (м, IH), 2.91-3.02 (м, 2H), 3.50-3.64 (м, IH), 3.74 (с, 3H), 4.15 (т, J = 6.6 Гц, 2H), 4.35 (д, J = 5.1 Гц, IH), 6.72 (д, J = 8.6 Гц, 2H), 6.80 (д, J = 8.6 Гц, 2H), 7.02 (д, J = 8.6 Гц, IH), 7.15 (д, J = 7.8 Гц, 0.5H), 7.74 (д, J = 7.8 Гц, 0.5H). 2, ll-Dimethyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 112): Yield 72%. 1 H NMR (400 MHz, CDCl 3 ): 1.28-1.35 (m, IH), 1.83-1.95 (m, 2H), 2.20-2.39 (m, 2H), 2.32 (s, 3H), 2.46 (s, 3H), 2.60-2.70 (m, IH), 2.91-3.02 (m, 2H), 3.50-3.64 (m, IH), 3.74 (s, 3H), 4.15 (t, J = 6.6 Hz, 2H ), 4.35 (d, J = 5.1 Hz, IH), 6.72 (d, J = 8.6 Hz, 2H), 6.80 (d, J = 8.6 Hz, 2H), 7.02 (d, J = 8.6 Hz, IH), 7.15 (d, J = 7.8 Hz, 0.5H), 7.74 (d, J = 7.8 Hz, 0.5H).
5-[2-(4-Meтoкcифeнил)этил]-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 428): Выход 59%. 1H NMR (400 МГц, CDCl3): 1.28-1.39 (м, IH), 1.83-1.95 (м, 2H), 2,23-2,39 (м, 2H), 2.32 (с, 3H), 2.60-2.70 (м, IH), 2.92- 3.07 (м, 2H), 3.55-3.64 (м, IH), 3.74 (с, 3H), 4.18 (т, J = 6.6 Гц, 2H), 4.33 (д, J = 5.1 Гц, IH), 6.73 (д, J = 7.6 Гц, 2H), 6.81 (д, J = 7.6 Гц, 2H), 7.10-7.21 (м, 2H), 7.36 (д, J = 8.3 Гц, IH), 7.47 (д, J = 7.8 Гц, IH). 5- [2- (4-Methoxyphenyl) ethyl] -ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 428): Yield 59%. 1 H NMR (400 MHz, CDCl 3 ): 1.28-1.39 (m, IH), 1.83-1.95 (m, 2H), 2.23-2.39 (m, 2H), 2.32 (s, 3H), 2.60 -2.70 (m, IH), 2.92-3.07 (m, 2H), 3.55-3.64 (m, IH), 3.74 (s, 3H), 4.18 (t, J = 6.6 Hz, 2H), 4.33 (d, J = 5.1 Hz, IH), 6.73 (d, J = 7.6 Hz, 2H), 6.81 (d, J = 7.6 Hz, 2H), 7.10-7.21 (m, 2H), 7.36 (d, J = 8.3 Hz, IH ), 7.47 (d, J = 7.8 Hz, IH).
2,Зj8~Tpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Щ-пиpидo[4,3-6]индoл 2, Z j 8 ~ Trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-Щ-pyrido [4,3-6] indole
(соединение 54): Выход 29%. 1H ЯМР (400 Гц) δ 1.13 (д, ЗН, J=6.6 Гц), 2.22 (дд, IH, J=7.1, 15.9 Гц), 2.45 (с, ЗН), 2.47 (дд, IH), 2.49 (с, ЗН), 2.83 (м, IH), 3.01 (т, 2H, J=7.3 Гц), 3.70 (д, IH, J=HA Гц), 3.90 (д, IH, J=HA Гц), 4.22 (т, 2H, J=7.3 Гц), 7.02 (д, IH, J=8.0 Гц), 7.07 (д, 2H, J=6.8 Гц), 7.30 - 7.22 (м, 5 H), (compound 54): Yield 29%. 1 H NMR (400 Hz) δ 1.13 (d, 3H, J = 6.6 Hz), 2.22 (dd, IH, J = 7.1, 15.9 Hz), 2.45 (s, 3H), 2.47 (dd, IH), 2.49 ( s, 3H), 2.83 (m, IH), 3.01 (t, 2H, J = 7.3 Hz), 3.70 (d, IH, J = HA Hz), 3.90 (d, IH, J = HA Hz), 4.22 ( t, 2H, J = 7.3 Hz), 7.02 (d, IH, J = 8.0 Hz), 7.07 (d, 2H, J = 6.8 Hz), 7.30 - 7.22 (m, 5 H),
8-Фтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-l//-пиpидo[4,3-^]индoл 8-fluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-l // - pyrido [4,3 - ^] indole
(соединение 76): Выход 45%. 1H ЯМР (400 МГц, CDCl3) δ 1.13 (д, ЗН, J=6.3 Гц), 2.23 (дд, IH, J=IA, 15.9 Гц), 2.45 (с, ЗН), 2.47 (дд, IH), 2.81 (м, IH), 3.01 (т, 2H, J=IA Гц), 3.64 (д, IH, J=14.1 Гц), 3.85 (д, IH, J=14.1 Гц), 4.22 (т, 2H, J=IA Гц), 6.90 (ддд, IH, J=2.3, 8.8, 9.1 Гц), 7.04 (д, 2H, J=6.8 Гц), 7.09 (дд, IH, J=I. Ъ, 9.6 Гц), 7.18 (дд, IH, J=4.3, 8.8 Гц), 7.30 -(compound 76): Yield 45%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.13 (d, 3H, J = 6.3 Hz), 2.23 (dd, IH, J = IA, 15.9 Hz), 2.45 (s, 3H), 2.47 (dd, IH) , 2.81 (m, IH), 3.01 (t, 2H, J = IA Hz), 3.64 (d, IH, J = 14.1 Hz), 3.85 (d, IH, J = 14.1 Hz), 4.22 (t, 2H, J = IA Hz), 6.90 (ddd, IH, J = 2.3, 8.8, 9.1 Hz), 7.04 (d, 2H, J = 6.8 Hz), 7.09 (dd, IH, J = I. B, 9.6 Hz), 7.18 (dd, IH, J = 4.3, 8.8 Hz), 7.30 -
7.24 (м, 3 H). 7.24 (m, 3 H).
2,3-Димeтил-5-(2-фeнилэтил)-2,3>4,5-тeтpaгидpo-l//_пиpидo[4,3-/,]индoл (соединение2,3-Dimethyl-5- (2-phenylethyl) -2,3 > 4,5-tetrahydro-l // _ pyrido [4,3 - /,] indole (compound
48): Выход 41%. 1H ЯМР (400 МГц, CDCl3) δ 1.14 (д, ЗН, J=6.3 Гц), 2.25 (дд, IH, J=IA, 15.9 Гц), 2.46 (с, ЗН), 2.50 (дд, IH, J=4.3, 15.9. Гц), 2.84 (м, IH), 3.03 (т, 2H, J=7.3 Гц), 3.72 (д, IH, JИ4.1 Гц), 3.92 (д, IH, J=14.1 Гц), 4.25 (т, 2H, J=7.3 Гц), 7.07 (д, 2H), 7.11 (т, IH), 7.19 (т, IH), 7.30 - 7.24 (м, 3 H), 7.34 (д, IH), 7.46 (д, IH). 48): Yield 41%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.14 (d, 3H, J = 6.3 Hz), 2.25 (dd, IH, J = IA, 15.9 Hz), 2.46 (s, 3H), 2.50 (dd, IH, J = 4.3, 15.9. Hz), 2.84 (m, IH), 3.03 (t, 2H, J = 7.3 Hz), 3.72 (d, IH, JI 4.1 Hz), 3.92 (d, IH, J = 14.1 Hz ), 4.25 (t, 2H, J = 7.3 Hz), 7.07 (d, 2H), 7.11 (t, IH), 7.19 (t, IH), 7.30 - 7.24 (m, 3 H), 7.34 (d, IH ), 7.46 (d, IH).
8-Meтoкcи-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lД-пиpидo[4,3-^]индoл (соединение 70): Выход 25%. 1H ЯМР (400 МГц, CDCl3) δ 1.13 (д, ЗН, J-6.6 Гц), 2.23 (дд, 8-Methoxy-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-l-pyrido [4.3 - ^] indole (compound 70): Yield 25%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.13 (d, 3H, J-6.6 Hz), 2.23 (dd,
83 83
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) IH, J=7.1, 15.9 Гц), 2.47 (с, 3H), 2.49 (дд, IH), 2.84 (м, IH), 3.02 (т, 2H, J=7.1 Гц), 3.70 (д,SUBSTITUTE SHEET (RULE 26) IH, J = 7.1, 15.9 Hz), 2.47 (s, 3H), 2.49 (dd, IH), 2.84 (m, IH), 3.02 (t, 2H, J = 7.1 Hz), 3.70 (d,
IH, J=14.1 Гц), 3.90 (с, 3H), 3.90 (д, IH, J=14.1 Гц), 4.21 (т, 2H, J=7.1 Гц), 6.86 (дд, IH, J=1.6, 8.8 Гц), 6.95 (д, IH, J=1.6 Гц), 7.07 (д, 2H, J=7.3 Гц), 7.22 (д, IH, J=8.9 Гц), 7.31 - 7.25 (м, 5 H). IH, J = 14.1 Hz), 3.90 (s, 3H), 3.90 (d, IH, J = 14.1 Hz), 4.21 (t, 2H, J = 7.1 Hz), 6.86 (dd, IH, J = 1.6, 8.8 Hz), 6.95 (d, IH, J = 1.6 Hz), 7.07 (d, 2H, J = 7.3 Hz), 7.22 (d, IH, J = 8.9 Hz), 7.31 - 7.25 (m, 5 H).
8-Xлop-2,3-димeтил-5-(2-фeнилэтил)-2,3?4,5-тeтpaгидpo-lH-пиpидo[4,3-6]индoл 8-chlorop-2,3-dimethyl-5- (2-phenylethyl) -2.3 ? 4,5-tetrahydro-lH-pyrido [4,3-6] indole
(соединение 79): Выход 31%. 1H ЯМР (400 МГц, CDCf3) δ 1.11 (д, ЗН, J=6.6 Гц), 2.21 (дд, IH, J=7.1, 15.9 Гц), 2.44 (с, ЗН), 2.46 (дд, IH), 2.79 (м, IH), 3.00 (т, 2H, J=7.3 Гц), 3.63 (д, IH, J=14.4 Гц), 3.84 (д, IH, J=14.4 Гц), 4.22 (т, 2H, J=7.3 Гц), 7.01 (д, 2H), 7.10 (дд, IH, J=I.7, 8.6 Гц), 7.18 (д, 1H, J=8.6 Гц), 7.30 - 7.24 (м, 3 H), 7.40 (д, IH, J=I.7 Гц). (compound 79): Yield 31%. 1 H NMR (400 MHz, CDCf 3 ) δ 1.11 (d, 3H, J = 6.6 Hz), 2.21 (dd, IH, J = 7.1, 15.9 Hz), 2.44 (s, 3H), 2.46 (dd, IH) , 2.79 (m, IH), 3.00 (t, 2H, J = 7.3 Hz), 3.63 (d, IH, J = 14.4 Hz), 3.84 (d, IH, J = 14.4 Hz), 4.22 (t, 2H, J = 7.3 Hz), 7.01 (d, 2H), 7.10 (dd, IH, J = I.7, 8.6 Hz), 7.18 (d, 1H, J = 8.6 Hz), 7.30 - 7.24 (m, 3 H) 7.40 (d, IH, J = I.7 Hz).
2,3,8-Tpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lЯ-пиpидo[4,3-6]индoл (соединение 181): Выход 24%. 1H ЯМР (400 МГц, CDCl3) δ 1.14 (д, ЗН, J=6.6 Гц), 2.24 (дд, IH), 2.24 (с, ЗН), 2.45 (с, ЗН), 2.47 (дд, IH), 2.48 (с, ЗН), 2.50 (м, IH), 2.84 (м, IH), 3.01 (т, 2H, J=7.3 Гц), 3.70 (д, IH, J=14.4 Гц), 3.90 (д, IH, J=14.4 Гц), 4.19 (т, 2H, J=7.3 Гц), 7.24 - 7.01 (м, 7H). 2,3,8-Trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-l-pyrido [4.3-6] indole (compound 181): Yield 24% . 1 H NMR (400 MHz, CDCl 3 ) δ 1.14 (d, 3H, J = 6.6 Hz), 2.24 (dd, IH), 2.24 (s, 3H), 2.45 (s, 3H), 2.47 (dd, IH) , 2.48 (s, 3H), 2.50 (m, IH), 2.84 (m, IH), 3.01 (t, 2H, J = 7.3 Hz), 3.70 (d, IH, J = 14.4 Hz), 3.90 (d, IH, J = 14.4 Hz), 4.19 (t, 2H, J = 7.3 Hz), 7.24 - 7.01 (m, 7H).
5-[2-(4-Фтopфeнил)этил]-2,358-тpимeтил-2,3,4,5-тeтpaгидpo-l/У-пиpидo[4,3-6]индoл5- [2- (4-Fluorophenyl) ethyl] -2.3 5 8-trimethyl-2,3,4,5-tetrahydro-l / U-pyrido [4,3-6] indole
(соединение 284): Выход 13%. 1H ЯМР (400 МГц, CDQ3) δ 1.15 (д, ЗН, J=6.6 Гц), 2.20 (дд, IH, J=6.8, 15.9 Гц), 2.47 (с, ЗН), 2.47 (дд, IH), 2.48 (с, ЗН), 2.89 (м, IH), 3.00 (т, 2H, J=6.8 Гц), 3.73 (д, IH, J=14.4 Гц), 3.91 (д, IH, J=14.4 Гц), 4.19 (т, 2H, J=7.1 Гц), 6.96 - 6.92 (м, 4H), 7.02 (д, IH, J=8.3 Гц), 7.19 (д, 2H, J=8.3 Гц), 7.24 (с, IH). (compound 284): Yield 13%. 1 H NMR (400 MHz, CDQ 3 ) δ 1.15 (d, 3H, J = 6.6 Hz), 2.20 (dd, IH, J = 6.8, 15.9 Hz), 2.47 (s, 3H), 2.47 (dd, IH) , 2.48 (s, 3H), 2.89 (m, IH), 3.00 (t, 2H, J = 6.8 Hz), 3.73 (d, IH, J = 14.4 Hz), 3.91 (d, IH, J = 14.4 Hz) 4.19 (t, 2H, J = 7.1 Hz), 6.96 - 6.92 (m, 4H), 7.02 (d, IH, J = 8.3 Hz), 7.19 (d, 2H, J = 8.3 Hz), 7.24 (s, IH).
5-[2-(4-Meтoкcифeнил)этил]-2,3,8-тpимeтил-2,3)4,5-тeтpaгидpo-l/-r-пиpидo[4,3-6]индoл (соединение 393): Выход 31%. 1H ЯМР (400 МГц, CDCl3) δ 1.14 (д, ЗН, J=6.6 Гц), 2.23 (дд, IH, J=6.8, 15.9 Гц), 2.46 (с, ЗН), 2.49 (с, ЗН), 2.52 (дд, IH), 2.86 (м, IH), 2.96 (т, 2H, J=7.1 Гц), 3.71 (д, IH, J=14.4 Гц), 3.80 (с, ЗН), 3.90 (д, IH, J=14.4 Гц), 4.18 (т, 2H, J=7.1 Гц), 6.82 (д, IH, J=8.3 Гц), 6.98 (д, 2H, J=8.3 Гц), 7.02 (д, IH, J=7.8 Гц), 7.25 - 7.22 (м, 2H). 5- [2- (4-Methoxyphenyl) ethyl] -2,3,8-trimethyl-2,3) 4,5-tetrahydro-l / - r- pyrido [4,3-6] indole (compound 393): Yield 31%. 1 H NMR (400 MHz, CDCl 3 ) δ 1.14 (d, 3H, J = 6.6 Hz), 2.23 (dd, IH, J = 6.8, 15.9 Hz), 2.46 (s, 3H), 2.49 (s, 3H) , 2.52 (dd, IH), 2.86 (m, IH), 2.96 (t, 2H, J = 7.1 Hz), 3.71 (d, IH, J = 14.4 Hz), 3.80 (s, 3H), 3.90 (d, IH, J = 14.4 Hz), 4.18 (t, 2H, J = 7.1 Hz), 6.82 (d, IH, J = 8.3 Hz), 6.98 (d, 2H, J = 8.3 Hz), 7.02 (d, IH, J = 7.8 Hz), 7.25 - 7.22 (m, 2H).
ll-Циклoгeкcил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 811): выход 5%, ЯМР 1H (CDCl3i δ, м.д.): 0.86- 1.03 (м, IH), 1.04-1.39 (м, 5H), 1.52-1.60 (м, IH), 1.68-1.77 (м, IH), 1.77-1.86 (м, 2H), 1.92- 2.11 (м, 2H), 1.98 (д, 2J= 16.6 Гц, IH), 2.44-2.57 (м, 2H), 2.58-2.67 (м,'lH), 2.74-2.86 (м, IH), 3.06-3.19 (м, 2H), 4.12-4.18 (м, IH), 4.20-4.29 (м, IH), 4.30-4.40 (м, IH), 5.01 (д, 3J= 5.6 Гц, IH), 6.84-6.8 (м, 2H), 7.18-7.25 (м, 4H), 7.28-7.34 (м, IH), 7.43-7.50 (м, 2H). ll-Cyclohexyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 811): 5% yield, 1 H NMR (CDCl 3i δ, ppm): 0.86-1.03 (m, IH), 1.04-1.39 (m, 5H), 1.52-1.60 (m, IH), 1.68-1.77 (m, IH), 1.77-1.86 (m, 2H), 1.92-2.11 (m, 2H), 1.98 (d, 2 J = 16.6 Hz, IH), 2.44-2.57 (m, 2H), 2.58-2.67 (m, ' lH), 2.74-2.86 (m, IH), 3.06-3.19 (m, 2H), 4.12-4.18 (m, IH), 4.20-4.29 (m, IH), 4.30-4.40 (m, IH), 5.01 (d, 3 J = 5.6 Hz, IH ), 6.84-6.8 (m, 2H), 7.18-7.25 (m, 4H), 7.28-7.34 (m, IH), 7.43-7.50 (m, 2H).
ll-Бeнзил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10-эпиминoциклoгeптa[6]индoл (соединение 812): выход 50%, ЯМР 1H (CDCl3, δ, м.д.): 1.25-1.35 (м, IH), 1.81-1.87 (м, IH), 1.88 (д, 2J = 16.5 Гц, IH), 2.18-2.30 (м, 2H), 2.69 (дд, 2J = 16.5, 3J= 4.3 Гц, IH), 3.11 (т, 3J = 6.7 Гц, 2H), 3.45 (д, 2J= 13.1 Гц, IH), 3.59 (д, 2J= 13.1 Гц, IH), 3.59-3.64 (м, IH), 4.22 (д, 3J ll-Benzil-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocycloheptol [6] indole (compound 812): 50% yield, 1 H NMR (CDCl 3 , δ, ppm): 1.25-1.35 (m, IH), 1.81-1.87 (m, IH), 1.88 (d, 2 J = 16.5 Hz, IH), 2.18-2.30 (m, 2H), 2.69 (dd, 2 J = 16.5, 3 J = 4.3 Hz, IH), 3.11 (t, 3 J = 6.7 Hz, 2H), 3.45 (d, 2 J = 13.1 Hz, IH), 3.59 (d, 2 J = 13.1 Hz, IH), 3.59-3.64 (m, IH), 4.22 (d, 3 J
84 84
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) = 4.3 Гц, IH), 4.22-4.36 (м, 2H), 6.94-6.99 (м, 2H), 7.11-7.17 (м, IH), 7.18-7.34 (м, ЮН), 7.43 (д, 3J= 8.6 Гц, IH). SUBSTITUTE SHEET (RULE 26) = 4.3 Hz, IH), 4.22-4.36 (m, 2H), 6.94-6.99 (m, 2H), 7.11-7.17 (m, IH), 7.18-7.34 (m, UN), 7.43 (d, 3 J = 8.6 Hz, IH).
ll-Meтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-5Я-7,ll- эпиминoциклooктa[6]индoл (соединение 111): выход 51%, ЯМР 1H (CDCl3, δ, м.д.): 0.97- 1.15 (м, IH, CH2), 1.33-1.47 (м, 2H, CH2), 1.79 (уш.д, 2J = 14.1 Гц, IH, CH2), 2.03 (д, 2J = 12.5 Гц, IH, CH2), 2.38-2.69 (м, ЗН, CH2), 2.52 (с, ЗН, CH3), 3.12 (т, 3J = 6.0 Гц, 2H, CH2), 3.60-3.68 (м, IH, CHN), 4.32 (тд, 3J = 6.0, 4J = 2.0 Гц, 2H, CH2), 4.68 (уш.с, IH, CH), 6.86- 6.94 (м, 2H, CH), 7.15-7.21 (м, ЗН, CH), 7.27-7.33 (м, 2H, CH), 7.38 (уш.д, 3J = 8.0 Гц, IH, CH), 7.45 (уш.д, 3J= 8.2 Гц, IH, CH). ll-Methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-5Y-7, ll-epiminocyclooct [6] indole (compound 111): 51% yield, 1 H NMR ( CDCl 3, δ, ppm): 0.97-1.15 (m, IH, CH 2 ), 1.33-1.47 (m, 2H, CH 2 ), 1.79 (br.s, 2 J = 14.1 Hz, IH, CH 2 ), 2.03 (d, 2 J = 12.5 Hz, IH, CH 2 ), 2.38-2.69 (m, ЗН, CH 2 ), 2.52 (s, ЗН, CH 3 ), 3.12 (t, 3 J = 6.0 Hz , 2H, CH 2 ), 3.60-3.68 (m, IH, CHN), 4.32 (td, 3 J = 6.0, 4 J = 2.0 Hz, 2H, CH 2 ), 4.68 (br.s, IH, CH), 6.86-6.94 (m, 2H, CH), 7.15-7.21 (m, 3H, CH), 7.27-7.33 (m, 2H, CH), 7.38 (br.s, 3 J = 8.0 Hz, IH, CH), 7.45 (br.s., 3 J = 8.2 Hz, IH, CH).
2,3,8-Tpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-l/Г-пиpидo[4,3-6]индoл (соединение 128): Выход 17%. 1H ЯМР (400 МГц, CDCl3) δ 1.13 (д, ЗН, J=6.3 Гц), 2.22 (дд, IH, J=T Л, 15.7 Гц), 2.35 (с, ЗН), 2.46 (с, ЗН), 2.49 (с, ЗН), 2.49 (дд, IH), 2.84 (м, IH), 2.97 (т, 2H, J=7.1 Гц), 3.67 (д, 1H, J=14.1 Гц), 3.87 (д, 1H, J=14.Г Гц), 4.19 (т, 2H, J=7.1 Гц), 6.98 (д, IH, J=7.6 Гц), 7.02 (д, 2H, J=8.3 Гц), 7.10 (д, IH, J=7.6 Гц), 7.25 - 7.22 (м, 2H). 2,3,8-Trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-l / G-pyrido [4.3-6] indole (compound 128): Yield 17% 1 H NMR (400 MHz, CDCl 3 ) δ 1.13 (d, 3H, J = 6.3 Hz), 2.22 (dd, IH, J = T L, 15.7 Hz), 2.35 (s, 3H), 2.46 (s, 3H ), 2.49 (s, 3H), 2.49 (dd, IH), 2.84 (m, IH), 2.97 (t, 2H, J = 7.1 Hz), 3.67 (d, 1H, J = 14.1 Hz), 3.87 (d , 1H, J = 14.H Hz), 4.19 (t, 2H, J = 7.1 Hz), 6.98 (d, IH, J = 7.6 Hz), 7.02 (d, 2H, J = 8.3 Hz), 7.10 (d , IH, J = 7.6 Hz), 7.25 - 7.22 (m, 2H).
2,ll-Димeтил-5-(2-(4-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[£>] индол (соединение 813): Выход 55%, спектр 1H ЯМР (400 МГц, CDCl3): 1.30-1.35 (м, IH), 1.84-1.91 (м, 2H), 2.29 (с, ЗН, CH3-N), 2.30 (с, ЗН, CH3-Ph), 2.31- 2.36 (м, 2H), 2.49 (с, ЗН, CH3-Ar), 2.66 (дд, J = 16.6 Гц, J = 3.5 Гц, IH), 2.95-3.01 (м, 2H), 3.51-3.55 (м, IH), 4.18 (т, J = 6.8 Гц, 2H, CH2-Ph), 4.27 (д, J = 5.3 Гц, IH), 6.62-6.65 (м, 2H), 7.01-7.05 (м, ЗН), 7.26-7.29 (м, 2H). 2, ll-Dimethyl-5- (2- (4-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocycloheptide [£>] indole (compound 813): Yield 55 %, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.30-1.35 (m, IH), 1.84-1.91 (m, 2H), 2.29 (s, 3H, CH 3 -N), 2.30 (s, 3H, CH 3 -Ph), 2.31- 2.36 (m, 2H), 2.49 (s, 3H, CH 3 -Ar), 2.66 (dd, J = 16.6 Hz, J = 3.5 Hz, IH), 2.95-3.01 (m, 2H), 3.51-3.55 (m, IH), 4.18 (t, J = 6.8 Hz, 2H, CH 2 -Ph), 4.27 (d, J = 5.3 Hz, IH), 6.62-6.65 (m, 2H), 7.01-7.05 (m, 3H); 7.26-7.29 (m, 2H).
2,ll-Димeтил-5-(2-(2-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 814): Выход 52%, спектр 1H ЯМР (400 МГц, CDCl3): 1.31-1.40 (м, IH), 1.82-1.88 (м, 2H), 2.129 (с, 3H^ CH3-Ph), 2.20-2.28 (м, IH), 2.30 (с, ЗН, CH3-N), 2.33-2.37 (м, IH), 2.49 (с, ЗН, CH3-Ar), 2.64 (дд, J = 15.8 Гц, J = 4.2 Гц, IH), 3.02-3.07 (м, 2H), 3.52-3.55 (м, IH), 4.20 (т, J = 6.8 Гц, 2H, CH2-Ph), 4.28 (д, J = 5.5 Гц, IH), 6.85-6.86 (м, IH), 7.02-7.07 (м, 2H), 7.10-7.14 (м, 2H), 7.26-7.29 (м, 2H). 2, ll-Dimethyl-5- (2- (2-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 814): Yield 52% spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.31-1.40 (m, IH), 1.82-1.88 (m, 2H), 2.129 (s, 3H ^ CH 3 -Ph), 2.20-2.28 (m, IH ), 2.30 (s, 3H, CH 3 -N), 2.33-2.37 (m, IH), 2.49 (s, 3H, CH 3 -Ar), 2.64 (dd, J = 15.8 Hz, J = 4.2 Hz, IH ), 3.02-3.07 (m, 2H), 3.52-3.55 (m, IH), 4.20 (t, J = 6.8 Hz, 2H, CH 2 -Ph), 4.28 (d, J = 5.5 Hz, IH), 6.85 -6.86 (m, IH), 7.02-7.07 (m, 2H), 7.10-7.14 (m, 2H), 7.26-7.29 (m, 2H).
2,ll-Димeтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>]индoл (соединение 815): Выход 61%, спектр 1H ЯМР (400 МГц, CDCl3): 1.30-1.35 (м, IH), 1.81-1.89 (м, 2H), 2.21-2.24 (м, IH), 2.28 (с, ЗН, CH3-N), 2.30-2.33 (м, IH), 2.49 (с, ЗН, CH3-Ar), 2.70 (дд, J = 16.3 Гц, J = 4.3 Гц, IH), 2.98-3.07 (м, 2H), 3.49- 3.52 (м, IH), 4.16-4.22 (м, ЗН), 6.86-6.93 (м, 4H), 7.01-7.03 (м, IH), 7.22-7.25 (м, IH), 7.29 (bс, IH) 2, ll-Dimethyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepto [/>] indole (compound 815): Yield 61 %, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.30-1.35 (m, IH), 1.81-1.89 (m, 2H), 2.21-2.24 (m, IH), 2.28 (s, 3H, CH 3 - N), 2.30-2.33 (m, IH), 2.49 (s, 3Н, CH 3 -Ar), 2.70 (dd, J = 16.3 Hz, J = 4.3 Hz, IH), 2.98-3.07 (m, 2H), 3.49- 3.52 (m, IH), 4.16-4.22 (m, ЗН), 6.86-6.93 (m, 4H), 7.01-7.03 (m, IH), 7.22-7.25 (m, IH), 7.29 (bс, IH )
2,ll-Димeтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 816): Выход 45%, спектр 1H ЯМР (400 МГц, CDCl3): 1.35-1.38 (м, IH), 1.89-1.95 (м, 2H), 2.29-2.34 (м, IH), 2.36 (c; ЗH, CH3-N), 2.42-2.45 2, ll-Dimethyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole (compound 816): Yield 45% spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.35-1.38 (m, IH), 1.89-1.95 (m, 2H), 2.29-2.34 (m, IH), 2.36 (s; 3H, CH 3 -N ), 2.42-2.45
85 85
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) (м, IH), 2.47 (с, ЗН, CH3-Ar), 2.71 (дц, J = 16.8 Гц, J = 4.3 Гц, IH), 3.00-3.06 (м, 2H), 3.67- 3.70 (м, IH), 4.19 (т, J = 6.8 Гц, 2H, CH2-Ph), 4.41 (д, J = 5.5 Гц, IH), 6.79-6.82 (м, 2H), 7.03-SUBSTITUTE SHEET (RULE 26) (m, IH), 2.47 (s, 3H, CH 3 -Ar), 2.71 (dts, J = 16.8 Hz, J = 4.3 Hz, IH), 3.00-3.06 (m, 2H), 3.67- 3.70 (m, IH), 4.19 (t, J = 6.8 Hz, 2H, CH 2 -Ph), 4.41 (d, J = 5.5 Hz, IH), 6.79-6.82 (m, 2H), 7.03-
7.06 (м, IH), 7.14-7.17 (м, 2H), 7.24-7.27 (м, 2H). 7.06 (m, IH), 7.14-7.17 (m, 2H), 7.24-7.27 (m, 2H).
ll-Meтил-5-(2-(4-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол (соединение 817): Выход 61%, спектр 1H ЯМР (400 МГц, CDCl3): 1.30-1.39 (м, IH), 1.86-1.91 (м, 2H), 2.23-2.25 (м, IH), 2.29 (с, ЗН, CH3-Ph), 2.30 (с, ЗН, CH3-N), 2.31-2.35 (м, IH), 2.69 (дц, J = 16.4 Гц, J = 4.0 Гц, IH), 2.99-3.04 (м, 2H), 3.53-ll-Methyl-5- (2- (4-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole (compound 817): Yield 61%, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.30-1.39 (m, IH), 1.86-1.91 (m, 2H), 2.23-2.25 (m, IH), 2.29 (s, 3H, CH 3 -Ph) , 2.30 (s, 3Н, CH 3 -N), 2.31-2.35 (m, IH), 2.69 (dts, J = 16.4 Hz, J = 4.0 Hz, IH), 2.99-3.04 (m, 2H), 3.53-
3.56 (м, IH), 4.21 (т, J = 7.2 Гц, 2H, CH2-Ph), 4.29 (д, J = 5.3 Гц, IH), 6.83 (д, J = 8.1 Гц, 2H), 7.03 (д, J = 8.1 Гц, 2H), 7.12-7.22 (м, 2H), 7.39 (д, J = 7.8 Гц, IH), 7.49 (д, J = 7.8 Гц, IH). ll-Meтил-5-(2-(2-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[£>] индол (соединение 818): Выход 54%, спектр 1H ЯМР (400 МГц, CDCl3): 1.30-1.39 (м, IH), 1.84-1.92 (м, 2H), 2.11 (с, ЗН, CH3-Ph), 2.20-2.26 (м, IH), 2.30 (с, ЗН, CH3-N), 2.35-2.40 (м, IH), 2.65 (дд, J = 16.4 Гц, J = 4.0 Гц, IH), 3.06-3.09 (м, 2H), 3.54-3.56 (m, IH), 4.21 (t, J = 7.2 Hz, 2H, CH 2 -Ph), 4.29 (d, J = 5.3 Hz, IH), 6.83 (d, J = 8.1 Hz, 2H), 7.03 ( d, J = 8.1 Hz, 2H), 7.12-7.22 (m, 2H), 7.39 (d, J = 7.8 Hz, IH), 7.49 (d, J = 7.8 Hz, IH). ll-Methyl-5- (2- (2-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohept [£>] indole (compound 818): 54% yield, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.30-1.39 (m, IH), 1.84-1.92 (m, 2H), 2.11 (s, 3H, CH 3 -Ph), 2.20-2.26 (m, IH) , 2.30 (s, 3Н, CH 3 -N), 2.35-2.40 (m, IH), 2.65 (dd, J = 16.4 Hz, J = 4.0 Hz, IH), 3.06-3.09 (m, 2H), 3.54-
3.57 (м, IH), 4.23 (т, J = 6.7 Гц, 2H, CH2-Ph), 4.31 (д, J = 5.6 Гц, IH), 6.84-6.86 (м, IH), 7.05-3.57 (m, IH), 4.23 (t, J = 6.7 Hz, 2H, CH 2 -Ph), 4.31 (d, J = 5.6 Hz, IH), 6.84-6.86 (m, IH), 7.05-
7.07 (м, IH), 7.11-7.15 (м, ЗН), 7.19-7.21 (м, IH), 7.38 (д, J = 8.0 Гц, IH), 7.48 (д, J = 8.0 Гц, IH). 7.07 (m, IH), 7.11-7.15 (m, 3H), 7.19-7.21 (m, IH), 7.38 (d, J = 8.0 Hz, IH), 7.48 (d, J = 8.0 Hz, IH).
ll-Meтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9,10-гeкcaГидpo-7,10- эпиминoциклoгeптa[A]индoл (соединение 819): Выход 68%, спектр 1H ЯМР (400 МГц, CDCl3): 1.29-1.34 (м, IH), 1.86-1.92 (м, 2H), 2.28-2.30 (м, IH), 2.30 (с, ЗН, CH3-N), 2.40-2.42 (м, IH), 2.70 (дц, J = 16.4 Гц, J = 4.0 Гц, IH), 3.00-3.07 (м, 2H), 3.58-3.62 (м, IH), 4.20 (т, J = 6.7 Гц, 2H, CH2-Ph), 4.34 (д, J = 5.6 Гц, IH), 6.82-6.91 (м, 4H), 7.12-7.20 (м, 2H), 7.33 (д, J = 8.0 Гц, IH), 7.46 (д, J = 8.0 Гц, IH). ll-Methyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9,10-hexaHydro-7,10- epiminocyclohepta [A] indole (compound 819): Yield 68%, spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.29-1.34 (m, IH), 1.86-1.92 (m, 2H), 2.28-2.30 (m, IH), 2.30 (s, 3H, CH 3 -N), 2.40-2.42 (m, IH), 2.70 (dts, J = 16.4 Hz, J = 4.0 Hz, IH), 3.00-3.07 (m, 2H), 3.58-3.62 (m, IH), 4.20 (t, J = 6.7 Hz, 2H, CH 2 -Ph), 4.34 (d, J = 5.6 Hz, IH), 6.82-6.91 (m, 4H), 7.12-7.20 (m, 2H), 7.33 (d, J = 8.0 Hz, IH), 7.46 (d, J = 8.0 Hz, IH).
ll-Meтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл (соединение 820): Выход 42%, спектр 1H ЯМР (400 МГц, CDCl3): 1.32-1.34 (м, IH), 1.81-1.88 (м, 2H), 2.24-2.27 (м, IH), 2.27 (с, ЗН, CH3-N), 2.28-2.31 (м, IH), 2.73 (дд, J = 16.4 Гц, J = 4.0 Гц, IH), 2.99-3.08 (м, 2H), 3.48-3.52 (м, IH), 4.19-4.24 (м, ЗН), 6.85 (д, J = 8.4 Гц, 2H), 7.11-7.22 (м, 4H), 7.34 (д, J = 8.0 Гц, IH), 7.51 (д, J = 8.0 Гц, IH). ll-Methyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepta [6] indole (compound 820): Yield 42%, spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.32-1.34 (m, IH), 1.81-1.88 (m, 2H), 2.24-2.27 (m, IH), 2.27 (s, 3H, CH 3 -N), 2.28-2.31 (m, IH), 2.73 (dd, J = 16.4 Hz, J = 4.0 Hz, IH), 2.99-3.08 (m, 2H), 3.48-3.52 (m, IH), 4.19-4.24 (m, ZN), 6.85 (d, J = 8.4 Hz, 2H), 7.11-7.22 (m, 4H), 7.34 (d, J = 8.0 Hz, IH), 7.51 (d, J = 8.0 Hz, IH).
l,2-Димeтил-5-(2-фeнилэтил)-2,354,5-тeтpaгидpo-l/У-пиpидo[4,3-6]индoл (соединение 99): Выход 33%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.50 (д, J = 6.5 Гц, ЗН, CH3-CH), 2.39- 2.42 (м, 2H, CH2-Ph), 2.49 (с, ЗН, CH3-N), 2.67-2.72 (м, IH), 2.99-3.04 (м, ЗН), 3.83 (q, J - 6.5 Гц, IH, CH3-CH ), 4.23-4.27 (м, 2H, CH2-N|Пdoiyi), 7.02 (м, 2H, Ar-H), 7.12-7.26 (м, 5H, Ar- H), 7.36 (д, J = 7.4 Гц, IH, Ar-H), 7.53 (д, J= 7.4 Гц, IH, Ar-H). l, 2-Dimethyl-5- (2-phenylethyl) -2.3 5 4.5-tetrahydro-l / U-pyrido [4.3-6] indole (compound 99): Yield 33%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.50 (d, J = 6.5 Hz, 3H, CH 3 -CH), 2.39 - 2.42 (m, 2H, CH 2 -Ph), 2.49 (s, 3H, CH 3- N), 2.67-2.72 (m, IH), 2.99-3.04 (m, ЗН), 3.83 (q, J - 6.5 Hz, IH, CH 3 -CH), 4.23-4.27 (m, 2H, CH 2 -N | Пdo iyi), 7.02 (m, 2H, Ar-H), 7.12-7.26 (m, 5H, Ar-H), 7.36 (d, J = 7.4 Hz, IH, Ar-H), 7.53 (d , J = 7.4 Hz, IH, Ar-H).
l,2,8-Tpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-£>]индoл l, 2,8-Trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4.3- £>] indole
(соединение 100): Выход 39%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.49 (д, J = 6.6 Гц, ЗН, (Compound 100): Yield 39%. Spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.49 (d, J = 6.6 Hz, 3P,
86 86
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) CH3-CH), 2.36-2.39 (м, 2H, CH2-Ph), 2.48 (с, ЗН, CH3-N), 2.50 (с, 3H5-CH3-Ar), 2.65-2.69 (м, IH), 2.98-3.04 (м, ЗН), 3.80 (q, J- 6.6 Гц, IH, CH3-CH ), 4.22 (t, 2H, J= 7.0 Гц, CH2-N,ndoιyi), 7.02-7.04 (м, ЗН, Ar-H), 7.23-7.28 (м, 4, Ar-H), 7.32(c, IH, Ar-H). SUBSTITUTE SHEET (RULE 26) CH 3 -CH), 2.36-2.39 (m, 2H, CH 2 -Ph), 2.48 (s, 3H, CH 3 -N), 2.50 (s, 3H 5 -CH 3 -Ar), 2.65-2.69 (m , IH), 2.98-3.04 (m, ЗН), 3.80 (q, J-6.6 Hz, IH, CH 3 -CH), 4.22 (t, 2H, J = 7.0 Hz, CH 2 -N, ndo ι y i ), 7.02-7.04 (m, 3Н, Ar-H), 7.23-7.28 (m, 4, Ar-H), 7.32 (s, IH, Ar-H).
Присоединение 2-винилiiиpидинa  Joining 2-vinyliiiridine
1.0 ммоля замещенного индола (синтезированного по вышеприведенным методикам), 1.5 ммоля (0.16 г) 2-винилпиpидинa, 3 ммоля (0.16 г) метилата натрия в 1,5 мл ДМСО в замкнутом объеме при перемешивании нагревали при 150 0C в течение 12 часов. ДМСО и винилпиридин удаляли в вакууме при 3 мм, рт. ст., продукт экстрагировали из остатка CH2Cl2. Растворитель упаривали, остаток хроматографировали на SiO2 (60 mеsh) элюент CH3OH/CHC13 = 1/20. Основание растворяли в 5 мл этанола, прибавляли 1 мл 5% раствора HCl, упаривали в вакууме (10 м рт. ст.), кристаллизовали из ацетонитрила. 1.0 mmol of substituted indole (synthesized according to the above methods), 1.5 mmol (0.16 g) of 2-vinylpyridine, 3 mmol (0.16 g) of sodium methylate in 1.5 ml of DMSO in a closed volume were heated at 150 ° C with stirring for 12 hours. DMSO and vinyl pyridine were removed in vacuo at 3 mmHg. Art., the product was extracted from the residue CH 2 Cl 2 . The solvent was evaporated, the residue was chromatographed on SiO 2 (60 mesh), eluent CH 3 OH / CHC 1 3 = 1/20. The base was dissolved in 5 ml of ethanol, 1 ml of a 5% HCl solution was added, evaporated in vacuo (10 mH), crystallized from acetonitrile.
ll-Meтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эnиминoциклoreптa[Z>] индол (соединение 575): Выход 29 %. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.74-2.15 (м 2H), 2.24-2.60 (м ЗН), 2.94 (м 2H), 3.26-3.84 (м ЗН), 4.27 (м 2H); 4.62 (м 2H); 5.06 (м IH); 6.89-7.13 (м 2H); 7.28-7.62 (м 2H); 7.75-8.09 (м 2H); 8.51-8.74 (м IH); 8.70 (д 0.5H, J=6.0); 8.82 (д 0.5H, J=6.0); 11.07 (уш.с 0.5H), 11.61 (уш.с 0.5H). ll-Methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,9-hexahydro-7,10-eniminocyclorepta [Z>] indole (compound 575): Yield 29%. 1 H NMR spectrum (200 MHz, DMSO-d 6 ) 1.74-2.15 (m 2H), 2.24-2.60 (m 3 H), 2.94 (m 2 H), 3.26-3.84 (m 3 H), 4.27 (m 2H); 4.62 (m 2H); 5.06 (m IH); 6.89-7.13 (m 2H); 7.28-7.62 (m 2H); 7.75-8.09 (m 2H); 8.51-8.74 (m IH); 8.70 (d 0.5H, J = 6.0); 8.82 (d 0.5H, J = 6.0); 11.07 (br.s 0.5H), 11.61 (br.s 0.5H).
2,ll-Димeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол дигидрохлорид (соединение 576): Выход 17 %. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.74-2.15 (м 2H), 224-2.60 (м 5H), 2.94 (м ЗН), 3.26-3.84 (м ЗН), 4.27 (м 2H); 4.56 (м 2H); 5.01 (с IH); 6.76-7.02 (м IH); 7.13-7.49 (м 2H); 7.63-7.97 (м 2H); 8.25 (м IH); 8.69 (д 0.5H, J=5.0); 8.78 (д 0.5H, J=5.0); 10.76 (уш.с 0.5H), 11.30 (уш.с 0.5H). 2-Фтop-ll-мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [Λ] индол (соединение 578): Выход 19 %. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.65-2.20 (м 2H); 2.64 (д 2H, J=4.4); 2.86 (д 2H, J=3.1); 2.97-3.26 (м 2H); 3.34- 3.66 (м 2H); 4.28 (м IH); 4.57 (м 2H); 5.02 (м IH); 6.88-7.05 (мlН); 7.18-7.60 (м 2H); 7.62- 8.00 (м 2H); 8.25 (м IH); 8.68 (д 0.5H, J=5.0); 8.74 (д 0.5H, J=5.0); 10.71 (уш.с 0.5H), 11.23 (уш.с 0.5H). 2, ll-Dimethyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole dihydrochloride (compound 576): Yield 17 % 1 H NMR spectrum (200 MHz, DMSO-d 6 ) 1.74-2.15 (m 2H), 224-2.60 (m 5H), 2.94 (m 3H), 3.26-3.84 (m 3H), 4.27 (m 2H); 4.56 (m 2H); 5.01 (with IH); 6.76-7.02 (m IH); 7.13-7.49 (m 2H); 7.63-7.97 (m 2H); 8.25 (m IH); 8.69 (d 0.5H, J = 5.0); 8.78 (d 0.5H, J = 5.0); 10.76 (br.s 0.5H), 11.30 (br.s 0.5H). 2-Ftop-ll-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [Λ] indole (compound 578): Yield 19 % 1 H NMR Spectrum (200 MHz, DMSO-d 6 ) 1.65-2.20 (m 2H); 2.64 (d 2H, J = 4.4); 2.86 (d 2H, J = 3.1); 2.97-3.26 (m 2H); 3.34-3.66 (m 2H); 4.28 (m IH); 4.57 (m 2H); 5.02 (m IH); 6.88-7.05 (mlH); 7.18-7.60 (m 2H); 7.62-8.00 (m 2H); 8.25 (m IH); 8.68 (d 0.5H, J = 5.0); 8.74 (d 0.5H, J = 5.0); 10.71 (br s 0.5H), 11.23 (br s 0.5H).
2-Meтoкcи-ll-мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[A]индoл дигидрохлорид (соединение 577): Выход 3 %. Спектр H ЯМР (200 МГц, DMSOd6) 1.65-2.20 (м 2H); 2,61 (м 2H); 2.84 (с ЗН); 3,07 (м ЗН); 3.74 (с ЗН); 4.11-4.44 (м 2H); 4.54 (м 2H); 5.02 (м IH); 6.68 (м IH); ); 6.96-7.49 (м 2H); 7.66-7.97 (м 2H); 8.31 (м IH); 8.68 (д 0.5H, J=6.0); 8.78 (д 0.5H, J=6.0); 10.79 (уш.с 0.5H), 11.38 (уш.с 0.5H) 2-Methoxy-ll-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [A] indole dihydrochloride (compound 577): Yield 3% H NMR Spectrum (200 MHz, DMSOd 6 ) 1.65-2.20 (m 2H); 2.61 (m 2H); 2.84 (with AP); 3.07 (m ZN); 3.74 (with AP); 4.11-4.44 (m 2H); 4.54 (m 2H); 5.02 (m IH); 6.68 (m IH); ); 6.96-7.49 (m 2H); 7.66-7.97 (m 2H); 8.31 (m IH); 8.68 (d 0.5H, J = 6.0); 8.78 (d 0.5H, J = 6.0); 10.79 (br.s 0.5H), 11.38 (br.s 0.5H)
2,3,8-Tpимeтил-5-(2-пиpидин-2-илэтил)-2,3?4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл дигидрохлорид (соединение 537) Выход 25%. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.37 2,3,8-Trimethyl-5- (2-pyridin-2-yl-ethyl) -2.3 ? 4,5-tetrahydro-III-pyrido [4,3-b] indole dihydrochloride (compound 537) Yield 25%. 1 H NMR Spectrum (200 MHz, DMSO-d 6 ) 1.37
87 87
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) (д 1.5H, J=6): 1.45 (д 1.5H, J=6); 2.35 (с 3H); 2.50 (с 3H); 2.78 (с IH): 2.92 (м 2H); 3.47 (т 2H, J=7); 3.78 (м 0.5H); 3.97 (м 0.5H); 4.27 (м Ш)f 4.56 (т 2H, J=7); 6.93 (д IH, J=8); 7.20 (с IH); 7.36 (д IH, J=8); 7.77 (м 2H); 8.28 (м IH); 8.56 (д IH, J=5); 11.19 (уш.с 0.5H), 11.37 (уш.с 0.5H). SUBSTITUTE SHEET (RULE 26) (d 1.5H, J = 6): 1.45 (d 1.5H, J = 6); 2.35 (s 3H); 2.50 (s 3H); 2.78 (s IH): 2.92 (m 2H); 3.47 (t 2H, J = 7); 3.78 (m 0.5H); 3.97 (m 0.5H); 4.27 (m W) f 4.56 (t 2H, J = 7); 6.93 (d IH, J = 8); 7.20 (with IH); 7.36 (d IH, J = 8); 7.77 (m 2H); 8.28 (m IH); 8.56 (d IH, J = 5); 11.19 (br.s 0.5H), 11.37 (br.s 0.5H).
l,2-Димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-Z>]индoл l, 2-Dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-Z>] indole
(соединение 577), выход 31%, Спектр 1H ЯМР (400 МГц, CDCl3): 1.49 (д, J = 6.6 Гц, ЗН, CH3-CH), 2.48-2.53 (м, 5H, iпсl. 2.49 (с, ЗН, CH3-N)), 2.69-2.72 (м, IH), 3.03-3.20 (м, ЗН), 3.82 (q, J = 6.6 Гц, IH, CH3-CH ), 4.41-4.45 (м, 2H, CH2-N,ndoIyι), 6.76 (д, J = 7.6 Гц, IH, Ar- H), 7.07-717 (м, ЗН, Ar-H), 7.32 (д, J= 7.6 Гц, IH, Ar-H), 7.45-7.51 (м, 2H, Ar-H), 8.59 (д, J = 4.0 Гц, IH5 Ar-H). (compound 577), yield 31%, Spectrum 1 H NMR (400 MHz, CDCl 3 ): 1.49 (d, J = 6.6 Hz, 3H, CH 3 -CH), 2.48-2.53 (m, 5H, iPSl. 2.49 ( s, 3H, CH 3 -N)), 2.69-2.72 (m, IH), 3.03-3.20 (m, 3H), 3.82 (q, J = 6.6 Hz, IH, CH 3 -CH), 4.41-4.45 ( m, 2H, CH 2 -N, ndoIy ι), 6.76 (d, J = 7.6 Hz, IH, Ar-H), 7.07-717 (m, ЗН, Ar-H), 7.32 (d, J = 7.6 Hz , IH, Ar-H), 7.45-7.51 (m, 2H, Ar-H), 8.59 (d, J = 4.0 Hz, IH 5 Ar-H).
l,2,8-Tpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-l/r-пиpидo[4,3-6]индoл (соединение 561), выход 36%, спектр 1H ЯМР (400 МГц, CDCl3): 1.51 (д, J = 6.6 Гц, ЗН, CH3-CH), 2.45-2.52 (м, 8H, iпсl. 2.46 (с, ЗН, CH3-N) апd 2.50 (с, ЗН, CH3-Ar)), 2.73-2.76 (м, IH), 3.05-3.08 (м, IH), 3.18 (t, J = 6.8 Гц, 2H, CH2-Py), 3.88 (q, J = 6.6 Гц, IH, CH3-CH ), 4.40 (t, J= 6.8 Гц, 2H, CH2-Nlпdoiyi), 6.75 (д, J= 7.8 Гц, IH, Ar-H), 6.99 (д, J= 8.3 Гц, IH, Ar- H), 7.12-7.14 (м, IH, Ar-H), 7.22 (д, J = 8.3 Гц, IH, Ar-H), 7.26 (с, IH, Ar-H), 7.44-7.47 (м, IH, Ar-H), 8.59 (д, J= 4.1 Гц, IH, Ar-H). l, 2,8-Trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-l / r-pyrido [4,3-6] indole (compound 561), yield 36 %, 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.51 (d, J = 6.6 Hz, 3H, CH 3 -CH), 2.45-2.52 (m, 8H, iPSl. 2.46 (s, 3H, CH 3 - N) add 2.50 (s, 3H, CH 3 -Ar)), 2.73-2.76 (m, IH), 3.05-3.08 (m, IH), 3.18 (t, J = 6.8 Hz, 2H, CH 2 -Py) , 3.88 (q, J = 6.6 Hz, IH, CH 3 -CH), 4.40 (t, J = 6.8 Hz, 2H, CH 2 -N lпdo i y i), 6.75 (d, J = 7.8 Hz, IH, Ar-H), 6.99 (d, J = 8.3 Hz, IH, Ar-H), 7.12-7.14 (m, IH, Ar-H), 7.22 (d, J = 8.3 Hz, IH, Ar-H), 7.26 (s, IH, Ar-H), 7.44-7.47 (m, IH, Ar-H), 8.59 (d, J = 4.1 Hz, IH, Ar-H).
Присоединение 3-винилπиpидинa Attachment of 3-vinylpyridine
1.0 ммоля замещенного индола (синтезированного по вышеприведенным методикам), 1.5 ммоля (0.16 г) 3-винилпиpидинa, 3 ммоля (0.16 г) метилата натрия в 1,5 мл ДМСО в замкнутом объеме при перемешивании нагревали при 150 °C в течение 24 часов. ДМСО и винилпиридин удаляли в вакууме при 3 мм рт. ст., продукт экстрагировали из остатка CH2Cl2. Растворитель упаривали, остаток хроматографировали на SiO2 (60 mеsh) элюент CH3OH/CHC13 = 1/20. Основание растворяли в 5 мл этанола, прибавляли 1 мл 5% раствора HCl, упаривали в вакууме (10 м рт. ст.), кристаллизовали из ацетонитрила. 1.0 mmol of substituted indole (synthesized according to the above methods), 1.5 mmol (0.16 g) of 3-vinylpyridine, 3 mmol (0.16 g) of sodium methylate in 1.5 ml of DMSO in a closed volume were heated at 150 ° C for 24 hours with stirring. DMSO and vinyl pyridine were removed in vacuo at 3 mm Hg. Art., the product was extracted from the residue CH 2 Cl 2 . The solvent was evaporated, the residue was chromatographed on SiO 2 (60 mesh), eluent CH 3 OH / CHC 1 3 = 1/20. The base was dissolved in 5 ml of ethanol, 1 ml of a 5% HCl solution was added, evaporated in vacuo (10 mH), crystallized from acetonitrile.
ll-Meтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6]индoл днгидрохлорид. (соединение 631), Выход 7 %. Спектр 1H ЯМР (200 МГц, DMSOd6) 1.74-2.15 (м 2H), 2.24-2.60 (м ЗН), 2.94 (м 2H), 3.26-3.84 (м ЗН), 4.27 (м 2H); 4.62 (м 2H); 5.06 (м IH); 6.78-7.25 (м ЗН); 7.31-7.65 (м 1.5H); 7.69-8.04 (м IH); 8.16-8.52 (м IH); 8.59-8.99 (м 1.5H); 11.07 (уш.с 0.5H), 11.61 (уш.с 0.5H). ll-Methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepta [6] indole dinhydrochloride. (compound 631), Yield 7%. 1 H NMR spectrum (200 MHz, DMSOd 6 ) 1.74-2.15 (m 2H), 2.24-2.60 (m 3 H), 2.94 (m 2 H), 3.26-3.84 (m 3 H), 4.27 (m 2H); 4.62 (m 2H); 5.06 (m IH); 6.78-7.25 (m ZN); 7.31-7.65 (m 1.5H); 7.69-8.04 (m IH); 8.16-8.52 (m IH); 8.59-8.99 (m 1.5H); 11.07 (br.s 0.5H), 11.61 (br.s 0.5H).
2,ll-Димeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол диrидрохлорйд. (соединение 632), Выход 30 %. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.57-2.18 (м+с 5H), 2.34-2.65 (м ЗН), 2.92 (м 2H), 3,00-3.84 (м ЗН), 4.27 (м 2H); 4.41 (м 2H); 5.01 (м IH); 6.81 (д 0.5H,-J=8.1); 6.96 (д 0.5H, J=8.1); 7.10 (д 2, ll-Dimethyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepto [/>] indole dihydrochloride. (compound 632), Yield 30%. 1 H NMR spectrum (200 MHz, DMSO-d 6 ) 1.57-2.18 (m + s 5H), 2.34-2.65 (m 3H), 2.92 (m 2H), 3.00-3.84 (m 3H), 4.27 (m 2H); 4.41 (m 2H); 5.01 (m IH); 6.81 (d 0.5H, -J = 8.1); 6.96 (d 0.5H, J = 8.1); 7.10 (d
88  88
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) 0.5H, J=8.1); 7.24 (с 0.5H); 7.38 (м IH); 7.89 (м IH); 8,34 (д 0.5H, J=8.1); 8,31 (д 0.5H,SUBSTITUTE SHEET (RULE 26) 0.5H, J = 8.1); 7.24 (s 0.5H); 7.38 (m IH); 7.89 (m IH); 8.34 (d 0.5H, J = 8.1); 8.31 (d 0.5H,
J=8.1); 8.76 (м 2H);11.13 (уш.с 0.5H), 1152 (уш.с 0.5H). J = 8.1); 8.76 (m 2H); 11.13 (br s 0.5H), 1152 (br s 0.5H).
2-Фтop-ll-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[Z>] индол дигидрохлорид (соединение 634). Выход 29 %. Спектр 1H ЯМР (200 МГц, DMSOd6) 1.65-2.18 (м 2H), 2.34-2.66 (м 3H), 2.94 (м 2H), 3,09-3.39 (м 2.5H), 3,65 (м 0.5H); 4.28 (м IH); 4.44 (м 2H); 5.04 (с IH); 6.83 (т 0.5H, J= 7.7); 6.98 (т 0.5H, J=7.7); 7.17-7.46 (м 1.5H); 7.54 (м 0.5H); 7.86 (м IH); 8.25 (д 0.5H, J=7.7); 8.37 (д 0.5H, J=7.7); 8.74 (м 2H); 11.17 (уш.с 0.5H), 11.58 (уш.с 0.5H)л 2-Ftop-ll-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepto [Z>] indole dihydrochloride (compound 634). Yield 29%. 1 H NMR spectrum (200 MHz, DMSOd 6 ) 1.65-2.18 (m 2H), 2.34-2.66 (m 3H), 2.94 (m 2H), 3.09-3.39 (m 2.5H), 3.65 (m 0.5 H); 4.28 (m IH); 4.44 (m 2H); 5.04 (with IH); 6.83 (t 0.5H, J = 7.7); 6.98 (t 0.5H, J = 7.7); 7.17-7.46 (m 1.5H); 7.54 (m 0.5H); 7.86 (m IH); 8.25 (d 0.5H, J = 7.7); 8.37 (d 0.5H, J = 7.7); 8.74 (m 2H); 11.17 (br.s 0.5H), 11.58 (br.s 0.5H) l
2,3,8-Tpимeтил-5-(2-пиpидин-3-илэтил)-2,354,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл дигидрохлорид (соединение 593) Выход 23 %. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.34 (д 1.5H, J=6); 1.44 (д 1.5H, J=6); 2.08 (с 3H); 2.35 (с 3H); 2.77 (м IH); 2.90 (м 2H); 3.19 (т 2H, J=7); 3.76 (м 0.5H); 3.90 (м 0.5H); 4.28 (м IH); 4.41 (т 2H, J-7); 6.95 (д IH, J=8); 7.22 (с IH); 7.35 (д IH, J=8); 7.61 (м IH); 7.98 (м IH); 8.56 (м 2H); 11.53 (уш.с 0.5H), 11.70 (уш.с 0.5H). 2,3,8-Trimethyl-5- (2-pyridin-3-yl-ethyl) -2.3 5 4,5-tetrahydro-lH-pyrido [4,3-b] indole dihydrochloride (compound 593) Yield 23%. 1 H NMR Spectrum (200 MHz, DMSO-d 6 ) 1.34 (d 1.5H, J = 6); 1.44 (d 1.5H, J = 6); 2.08 (s 3H); 2.35 (s 3H); 2.77 (m IH); 2.90 (m 2H); 3.19 (t 2H, J = 7); 3.76 (m 0.5H); 3.90 (m 0.5H); 4.28 (m IH); 4.41 (t 2H, J-7); 6.95 (d IH, J = 8); 7.22 (with IH); 7.35 (d IH, J = 8); 7.61 (m IH); 7.98 (m IH); 8.56 (m 2H); 11.53 (br s 0.5H), 11.70 (br s 0.5H).
2,3-Димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл (соединение 588). Выход 21%. Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.54 (д 1.2 H, Me, J=6); 1.73 (д 1.8 H, Me J=6); 2.83 (с 1.2 H, MeN); 2.91 (с 1.8 H, MeN); 3.07 (м 1.8 H, CH2); 3.23 (м 2.2 H, CH2); 3.52 (м 1.4 H, CH2); 3.63 (м 0.6 H, CH2); 4.44 (м 2 H, CH2); 4.68 (м 0.6 H, CH) 4.81 (м 0.4 H, CH); 7.03 (м 2 H, CHAr); 7.42 (м 2 H, CHA1); 7.90 (м 1 H, СНдr); 8.38 (м 1 H, СНдr); 8.73 (м 2 H, СНдr); 11.41 (уш.с 0.6H), 11.64 (уш.с 0.4H). 2,3-Dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole (compound 588). Yield 21%. 1 H NMR spectrum (200 MHz, DMSO-d 6 ) 1.54 (d 1.2 H, Me, J = 6); 1.73 (d 1.8 H, Me J = 6); 2.83 (s 1.2 H, MeN); 2.91 (s 1.8 H, MeN); 3.07 (m 1.8 H, CH 2 ); 3.23 (m 2.2 H, CH 2 ); 3.52 (m 1.4 H, CH 2 ); 3.63 (m 0.6 H, CH 2 ); 4.44 (m 2 H, CH 2 ); 4.68 (m 0.6 H, CH); 4.81 (m 0.4 H, CH); 7.03 (m 2 H, CH Ar ); 7.42 (m 2 H, CH A1 ); 7.90 (m 1 H, CHDr); 8.38 (m 1 H, CHDr); 8.73 (m 2 H, CHDr); 11.41 (br s 0.6H), 11.64 (br s 0.4H).
l,2,8-Tpимeтил-5-(2-пиpидин-3-илэтил)-2,354,5-тeтpaгидpo-lH-пиpидo[4,3-b)индoл (соединение 617). Выход 22%. Спектр 1H ЯМР (200 МГц, DMSOd6): 1.53 (д 1.1 H, Me, J=6.2); 1.67 (д 1.9 H, Me J=6.2); 2.32 (с 3 H, Me); 2.83 (с 1.1 H, MeN); 2.89(c 1.9 H, MeN); 3.01 (м 2 H, CH2); 3.20 (м 2 H, CH2); 3.5 (м 1.3 H, CH2); 3.64 (м 0.7 H, CH2); 4.40 (м 2 H, CH2); 4.65 (м 0.6 H, CH) 4.80 (м 0.4 H, CH); 6.89 (д 1 H, CUM, J=I.9); 7.24 (м 2 H, CHAr); 7.92 (м 1 H, CHAr); 8.35 (д 1 H, CHAr, J=6.4); 8.71 (м 2 H, CHAr); 11.48 (уш.с 0.6H), 1 1.69 (уш.с 0.4H). l, 2,8-Trimethyl-5- (2-pyridin-3-yl-ethyl) -2.3 5 4,5-tetrahydro-lH-pyrido [4,3-b) indole (compound 617). Yield 22%. 1 H NMR Spectrum (200 MHz, DMSOd 6 ): 1.53 (d 1.1 H, Me, J = 6.2); 1.67 (d 1.9 H, Me J = 6.2); 2.32 (s 3 H, Me); 2.83 (s 1.1 H, MeN); 2.89 (c 1.9 H, MeN); 3.01 (m 2 H, CH 2 ); 3.20 (m 2 H, CH 2 ); 3.5 (m 1.3 H, CH 2 ); 3.64 (m 0.7 H, CH 2 ); 4.40 (m 2 H, CH 2 ); 4.65 (m 0.6 H, CH); 4.80 (m 0.4 H, CH); 6.89 (d 1 H, CU M , J = I.9); 7.24 (m 2 H, CH Ar ); 7.92 (m 1 H, CH Ar ); 8.35 (d 1 H, CH Ar , J = 6.4); 8.71 (m 2 H, CH Ar ); 11.48 (br s 0.6H), 1 1.69 (br s 0.4H).
Присоединение 4-винилпиpидинa  The addition of 4-vinylpyridine
1.0 ммоля замещенного индола (синтезированного по вышеприведенным методикам), 1.5 ммоля (0.16 г) 4-винилпиpидинa, 1 ммоля (0.15 г) CsF в 1,5 мл ДМСΘ в замкнутом объеме при перемешивании нагревали при 140°C в течение 6 часов. ДМСО и винилпиридин удаляли в вакууме при 3 мм рт. ст., продукт экстрагировали из остатка CH2Cl2. 1.0 mmol of substituted indole (synthesized according to the above methods), 1.5 mmol (0.16 g) of 4-vinylpyridine, 1 mmol (0.15 g) of CsF in 1.5 ml of DMSΘ in a closed volume were heated at 140 ° C for 6 hours with stirring. DMSO and vinyl pyridine were removed in vacuo at 3 mm Hg. Art., the product was extracted from the residue CH 2 Cl 2 .
Растворитель упаривали, остаток хроматографировали на SiO2 (60 mеsh) элюент The solvent was evaporated, the residue was chromatographed on SiO 2 (60 mesh) eluent
CH3OH/CHCI3 = 1/20. Основание растворяли в 5 мл этанола, прибавляли 1 мл 5% раствора HCl, упаривали в вакууме (10 м рт. ст.), кристаллизовали из ацетонитрила. CH 3 OH / CHCI 3 = 1/20. The base was dissolved in 5 ml of ethanol, 1 ml of a 5% HCl solution was added, evaporated in vacuo (10 mH), crystallized from acetonitrile.
89 89
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) ll-Meтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>]индoл дигидрохлорид (соединение 686). Выход 35 %. Спектр 1HSUBSTITUTE SHEET (RULE 26) ll-Methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepto [/>] indole dihydrochloride (compound 686). Yield 35%. Spectrum 1 H
ЯМР (200 МГц, DMSOd6) 1.73 (м IH); 2.05 (м IH); 2.90 (м 3H); 3.30 (м 5H); 4.25 (м 2H); 4.50 (т 2H, J= 7.0); 5.05 (д IH, J=4.4); 6.96-7.21 (м 2H); 7.25-7.62 (м 2H); 7.74 (д IH, J=6.0); 7.84 (д IH, J=6.0); 8.68 (д IH, J=6.0); 8.74 (д 2H, J=6.0); 10.95 (уш.с 0.5 H); 11.44 (уш.с 0.5H). NMR (200 MHz, DMSOd 6 ) 1.73 (m IH); 2.05 (m IH); 2.90 (m 3H); 3.30 (m 5H); 4.25 (m 2H); 4.50 (t 2H, J = 7.0); 5.05 (d IH, J = 4.4); 6.96-7.21 (m 2H); 7.25-7.62 (m 2H); 7.74 (d IH, J = 6.0); 7.84 (d IH, J = 6.0); 8.68 (d IH, J = 6.0); 8.74 (d 2H, J = 6.0); 10.95 (br.s 0.5 H); 11.44 (br s 0.5H).
2,ll-Димeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминоциклогепта [b] индол дигидpoxлopид(coeдинeниe 687). Выход 32 %. Спектр H ЯМР (200 МГц, DMSO-d6) 1.68 (м IH), 2.01 (м IH), 2.35 (д ЗН, J=4), 2.80 (м 3H), 3.30 (м 5H), 4.19 (м 2H); 4.44 (т 2H, J=7.0); 4.98 (д, 'lH, J=4); 6.80-7.01 (м IH); 7.13-7.43 (м 2H); 7.76 (д IH), J=6.0); 7.85 (д IH), J=6.0); 8.76 (д IH, J=6.0); 8.70 (д IH, J=6.0); 11.00 (уш.с 0.5H), 11.46 (уш.с 0.5H). 2, ll-Dimethyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole dihydroxlorid (coefficient 687). Yield 32%. H NMR spectrum (200 MHz, DMSO-d 6 ) 1.68 (m IH), 2.01 (m IH), 2.35 (d S, J = 4), 2.80 (m 3H), 3.30 (m 5H), 4.19 (m 2H ); 4.44 (t 2H, J = 7.0); 4.98 (d, ' lH, J = 4); 6.80-7.01 (m IH); 7.13-7.43 (m 2H); 7.76 (d IH), J = 6.0); 7.85 (d IH), J = 6.0); 8.76 (d IH, J = 6.0); 8.70 (d IH, J = 6.0); 11.00 (br.s 0.5H), 11.46 (br.s 0.5H).
2-Фтop-ll-мeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoreптa[Z>] индол дигидрохлорид (соединение 689). Выход 34 %. Спектр H ЯМР (200 МГц, DMSOd6) 1.73 (м IH); 2.02 (м IH); 2.45 (м IH); 2.86 (м ЗН); 3.34 (м ЗН), 3.67 (м IH); 4.25 (м 2H); 4.51 (т 2H, J= 7.0); 5.04 (д IH, J= 4.0); 6.91 (м IH); 7.20-7.60 (м 2H); 7.94 (м 2H); 8.72 (д IH, J=6.0); 8.83 (д IH, J=6.0); 11.30 (уш.с. 0.5H); 11.74 (уш.с. 0.5H). 2-Fluoro-ll-methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclorepta [Z>] indole dihydrochloride (compound 689). Yield 34%. H NMR Spectrum (200 MHz, DMSOd 6 ) 1.73 (m IH); 2.02 (m IH); 2.45 (m IH); 2.86 (m ZN); 3.34 (m ZN); 3.67 (m IH); 4.25 (m 2H); 4.51 (t 2H, J = 7.0); 5.04 (d IH, J = 4.0); 6.91 (m IH); 7.20-7.60 (m 2H); 7.94 (m 2H); 8.72 (d IH, J = 6.0); 8.83 (d IH, J = 6.0); 11.30 (br.s. 0.5H); 11.74 (br.s 0.5H).
2-Meтoкcи-ll-мeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[/>] индол дигидрохлорид (соединение 688). Выход 0.081 г (21 %). Спектр 1H ЯМР (200 МГц, DMSO-d6) 1.70 (м IH), 2.07 (м IH), 2.45 (м IH), 2.83 (м ЗН), 3.24 (м 4H), 3.77 (с+с ЗН); 4.21 (м 2H); 4.44 (т 2H, J=7.0); 5.02 (д IH, J=4.0); 6.72 (м IH); 7.00-7.47 (м 2H); 7.76 (д IH, J=6.0); 7.84 (д IH, J=6.0); 8.75 (м 2H); 1 1.30 (уш.с 0.5H), 11.74 (уш.с 0.5H). 2-Methoxy-ll-methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [/>] indole dihydrochloride (compound 688). Yield 0.081 g (21%). 1 H NMR spectrum (200 MHz, DMSO-d 6 ) 1.70 (m IH), 2.07 (m IH), 2.45 (m IH), 2.83 (m 3H), 3.24 (m 4H), 3.77 (s + s 3H) ; 4.21 (m 2H); 4.44 (t 2H, J = 7.0); 5.02 (d IH, J = 4.0); 6.72 (m IH); 7.00-7.47 (m 2H); 7.76 (d IH, J = 6.0); 7.84 (d IH, J = 6.0); 8.75 (m 2H); 1 1.30 (br s 0.5H), 11.74 (br s 0.5H).
2,3,8-Tpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-l//-пиpидo[4,3-6]индoл, (соединение 649) выход 17%. 1H ЯМР (400 Гц) δ 1.13 (д, ЗН, J=6.6 Гц), 2.21 (дд, IH, J=7.1, 15.9 Гц), 2.45 (с, ЗН), 2.47 (с, ЗН), 2.50 (дд, IH), 2.85 (м, IH), 3.01 (т, 2H, J=Tl Гц), 3.69 (д, IH, J=UA Гц), 3.88 (д, IH, J=UA Гц), 4.24 (т, 2H, J=IA Гц), 6.94 (д, 2H, J=5.8 Гц), 7.01 (д, IH, J=8.3 Гц), 7.17 (д, IH, J=8.3 Гц), 7.24 (с, IH), 8.47 (д, 2H, J=5.8 Гц). 2,3,8-Trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-l // - pyrido [4,3-6] indole, (compound 649) yield 17 % 1 H NMR (400 Hz) δ 1.13 (d, 3H, J = 6.6 Hz), 2.21 (dd, IH, J = 7.1, 15.9 Hz), 2.45 (s, 3H), 2.47 (s, 3H), 2.50 ( dd, IH), 2.85 (m, IH), 3.01 (t, 2H, J = Tl Hz), 3.69 (d, IH, J = UA Hz), 3.88 (d, IH, J = UA Hz), 4.24 ( t, 2H, J = IA Hz), 6.94 (d, 2H, J = 5.8 Hz), 7.01 (d, IH, J = 8.3 Hz), 7.17 (d, IH, J = 8.3 Hz), 7.24 (s, IH), 8.47 (d, 2H, J = 5.8 Hz).
8-Фтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-li/-пиpидo[4,3- 6]индoл, (соединение 660), выход 18%. 1H ЯМР (400 Гц) δ 1.12 (д, ЗН, J=6.3 Гц), 2.22 (дд, IH, J=I Л, 15.9 Гц), 2.45 (с, ЗН), 2.50 (дд, IH), 2.81 (м, IH), 3.00 (т, 2H, J=7.1 Гц), 3.61 (д, IH, J=14.4 Гц), 3.82 (д, IH, J=UA Гц), 4.24 (т, 2H, J=TA Гц), 6.90 (ддд, IH, J=2.3, 8.8, 9.1 Гц), 6.91 (д, 2H, J=5.8 Гц), 7.09 (дд, IH, J=I. Ъ, 9.6 Гц), 7.13 (дд, IH, 17=4.3, 8.8 Гц), 8.47 (д, 2H, J=5.8 Гц). 8-Fluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-li / pyrido [4,3-6] indole, (compound 660), yield 18%. 1 H NMR (400 Hz) δ 1.12 (d, 3H, J = 6.3 Hz), 2.22 (dd, IH, J = I L, 15.9 Hz), 2.45 (s, 3H), 2.50 (dd, IH), 2.81 (m, IH), 3.00 (t, 2H, J = 7.1 Hz), 3.61 (d, IH, J = 14.4 Hz), 3.82 (d, IH, J = UA Hz), 4.24 (t, 2H, J = TA Hz), 6.90 (ddd, IH, J = 2.3, 8.8, 9.1 Hz), 6.91 (d, 2H, J = 5.8 Hz), 7.09 (dd, IH, J = I. B, 9.6 Hz), 7.13 ( dd, IH, 17 = 4.3, 8.8 Hz), 8.47 (d, 2H, J = 5.8 Hz).
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) l,2,8-Tpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-l/-r-пиpидo[4,3-6]индoл, (соединение 672), выход 36%. Спектр 1H ЯМР (400 МГц, CDCl3): 1.51 (д, J = 6.6 Гц, ЗН, CH3-CH), 2.38-2.42 (м, 2H), 2.47 (с, ЗН, CH3-N), 2.50 (с, ЗН, CH3-Ar), 2.70-2.73 (м, IH), 2.99-3.06 (м, ЗН), 3.87 (q, J = 6.6 Гц, IH, CH3-CH ), 4.23 (t, J= 6.9 Гц, 2H, CH2-Nindoiyi), 6.88 (д, J= 5.2 Гц, 2H, Ar-H), 7.03 (д, J- 8.1 Гц, IH, Ar-H), 7:17 (д, J= 8.1 Гц, IH, Ar-H), 7.30 (с, IH, Ar-H), 8.46 (д, J= 5.2 Гц, 2H, Ar-H). SUBSTITUTE SHEET (RULE 26) l, 2,8-Trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-l / - r -pyrido [4,3-6] indole, (compound 672), yield 36%. 1 H NMR spectrum (400 MHz, CDCl 3 ): 1.51 (d, J = 6.6 Hz, 3H, CH 3 -CH), 2.38-2.42 (m, 2H), 2.47 (s, 3H, CH 3 -N), 2.50 (s, 3H, CH 3 -Ar), 2.70-2.73 (m, IH), 2.99-3.06 (m, 3H), 3.87 (q, J = 6.6 Hz, IH, CH 3 -CH), 4.23 (t , J = 6.9 Hz, 2H, CH 2 -Ni nd oiyi), 6.88 (d, J = 5.2 Hz, 2H, Ar-H), 7.03 (d, J-8.1 Hz, IH, Ar-H), 7: 17 (d, J = 8.1 Hz, IH, Ar-H), 7.30 (s, IH, Ar-H), 8.46 (d, J = 5.2 Hz, 2H, Ar-H).
Биологические испытания и активность синтезированных соединений  Biological tests and activity of synthesized compounds
Возможность осуществления изобретения с реализацией заявляемого назначения подтверждается, но не исчерпывается следующими сведениями. The possibility of carrying out the invention with the implementation of the claimed purpose is confirmed, but not limited to the following information.
Пример биo-1. Определение активности соединений общей формулы I по связыванию с серотониновым рецептором 5-HT6. Example bio-1. Determination of the activity of compounds of general formula I by binding to the 5-HT 6 serotonin receptor.
Для оценки веществ на их способность взаимодействовать с серотониновым рецептором 5-HT6 использовали метод радиqлигандного связывания. Для этого готовили мембранные препараты из клеток HeLa, экспрессирующих рекомбинантный человеческий 5-HT6 рецептор, путем гомогенизирования рекомбинантных клеток с последующим отделением плазматических мембран от ядер, митохондрий и клеточных фрагментов путем дифференциального центрифугирования. Определение связывания заявляемых соединений с 5-HT6 рецептором проводили в соответствии с методикой, описанной в [Мопsmа FJ Jr, Shen Y, Wаrd RP, Hamblin MW and Sibley DR, Сlопiпg апd ехрrеssiоп оf а поvеl sеrоtопiп rесерtоr with high аffmitу fоr triсусliс рsусhоtrорiс drugs. MoI Рhаrтасоl. 1993; 43: 320-327,]. Для этого мембранные препараты инкубировали с меченым лигандом (1.5 nM [3H] LSD) без и в присутствии исследуемых соединений в течение 120 минут при 37°C в среде, состоящей из 50 mМ Тris-НСl, рН 7.4, 150 mМ NaCl, 2 mМ Аsсоrbiс Асid, 0.001% BSA. Образцы после инкубации фильтровали под вакуумом на стекло- микроволоконных фильтрах G/F (Мilliроr, USA), фильтры трижды промывали холодным раствором среды и радиоактивность измеряли с помощью сцинтилляционного счетчика МiсrоВеtа 340 (РеrkiпЕlmеr, USA). Неспецифическое связывание, которое составляло 30% от общего связывания, определяли инкубацией мембранных препаратов с радиолигандом в присутствии 5 μМ Sеrоtопiп (5-HT). В качестве положительного контроля использовали Меthiоthерiп. Связывание тестируемых соединений с рецептором определялось по их способности вытеснять радиоактивный лиганд и выражалось в процентах вытеснения. Процент вытеснения определялся по следующей формуле: To evaluate substances for their ability to interact with the 5-HT 6 serotonin receptor, the radioligand binding method was used. For this, membrane preparations were prepared from HeLa cells expressing the recombinant human 5-HT 6 receptor by homogenizing the recombinant cells, followed by separation of the plasma membranes from nuclei, mitochondria, and cell fragments by differential centrifugation. The determination of the binding of the claimed compounds with the 5-HT 6 receptor was carried out in accordance with the procedure described in [Mopma FJ Jr, Shen Y, War RP, Hamblin MW and Sibley DR, Slipg apd expréssiopo f and po rve seropotopo rcipo trcopr . MoI Pharmacol. 1993; 43: 320-327,]. For this, membrane preparations were incubated with a labeled ligand (1.5 nM [ 3 H] LSD) without and in the presence of the test compounds for 120 minutes at 37 ° C in an environment consisting of 50 mM Tris-Hcl, pH 7.4, 150 mM NaCl, 2 mM Ascorbiis Acid, 0.001% BSA. After incubation, the samples were filtered under vacuum on G / F glass microfiber filters (Milliro, USA), the filters were washed three times with a cold solution of the medium, and radioactivity was measured using a MicroBet 340 scintillation counter (RekelPelmer, USA). Nonspecific binding, which accounted for 30% of total binding, was determined by incubating membrane preparations with a radioligand in the presence of 5 μM Serotopip (5-HT). As a positive control, Metiotherip was used. The binding of the test compounds to the receptor was determined by their ability to displace the radioactive ligand and was expressed as a percentage of displacement. The crowding out percentage was determined by the following formula:
%I = TA ~ CA * \00, % I = TA ~ CA * \ 00,
TA - NA  TA - NA
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) где ТА - это общая радиоактивность в присутствии только радиоактивного лиганда, CA - это радиоактивность в присутствии радиолиганда и тестируемого соединения и NA - это радиоактивность в присутствии радиолиганда и серотонина (5 μМ). SUBSTITUTE SHEET (RULE 26) where TA is the total radioactivity in the presence of only a radioactive ligand, CA is radioactivity in the presence of a radioligand and test compound, and NA is radioactivity in the presence of a radioligand and serotonin (5 μM).
Результаты испытаний некоторых соединений общей формулы I, представленные в таблице 1, свидетельствуют об активности этих соединений по отношению к 5-HT6 рецепторам. The test results of some compounds of General formula I, are presented in table 1, indicate the activity of these compounds in relation to 5-HT 6 receptors.
Таблица 1. Процент вытеснения меченого лиганда LSD, связанного с 5-HT6 рецепторами, под действием 1 мкМ заявляемого вещества  Table 1. The percentage of displacement of the labeled LSD ligand associated with 5-HT6 receptors under the action of 1 μm of the claimed substance
Figure imgf000094_0001
Figure imgf000094_0001
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) . SUBSTITUTE SHEET (RULE 26) .
Пример биo-2. Определение активности соединений общей формулы I по связыванию с серотониновым рецепторам 5-HT7. Example bio-2. Determination of the activity of compounds of general formula I by binding to serotonin receptors 5-HT 7 .
Для оценки веществ на их потенциальную способность взаимодействовать с серотониновым 5-HT7 рецептором использовали метод радиолигандного связывания. Для этого, сДНК человеческого 5-HT7 рецептора была экспрессирована в клетках CHO, как описано в [Shеп Y, Monsma FJ Jr, Меtсаlf MA, Jоsе P.A., Наmbliп M.W., Siblеу D.R. Моlесulаг сlопiпg апd ехрrеssiоп оf а 5-hydroxytгyptamine 7 sеrоtопiп rесерtог subtуре. J Вiоl Сhет. 1993; 268: 18200-18204]. Из трансфецированных таким образом клеток готовили мембранные препараты путем гомогенизирования клеточной суспензии с последующим отделением плазматических мембран от ядер, митохондрий и клеточных фрагментов путем дифференциального центрифугирования. Определение связывания изучаемых соединений с 5-HT7 рецептором проводили в соответствии с методикой, описанной в [Rоth B.L., Сrаigо S.C., Сhоudhаrу M.S., Uluег S., Monsma F.J., Shеп Y., Меltzеr H.Y., Siblеу D.R. Вiпdiпg оf tурiсаl апd аtурiсаl апtiрsусhоtiс аgепts tо 5-hydrαxytryptamiпe-6 апd 5- hydгoxytгyptamiпe-7 rесерtоrs. J Рhаrтасоl Ехр Тhеr. 1994; 268: 1403-1410]. В предпочтительном исполнении, клеточные мембраны инкубировали с меченым лигандом (5.5 nM [3H] LSD) без и в присутствии исследуемых соединений в течение 2 часов при 25°C в среде, состоящей из 50 mМ Тris-НСl, рН 7.4, 10 mМ MgCl2, 0.5 mМ EDTA. Образцы после инкубации фильтровали под вакуумом на стекло-микроволоконных фильтрах G/F (Мilliроr, USA), фильтры трижды промывали холодным раствором среды и радиоактивность измеряли с помощью сцинтилляционного счетчика МiсrоВеtа 340 (РеrkiпЕlmеr, USA). Неспецифическое связывание, которое составляло 10% от общего связывания, определяли инкубацией мембранных препаратов с радиолигандом в присутствии 10 μМ серотонина. To assess the substances for their potential ability to interact with the serotonin 5-HT 7 receptor, the radioligand binding method was used. For this, the human 5-HT 7 receptor cDNA was expressed in CHO cells, as described in [Schep Y, Monsma FJ Jr, Metals MA, José PA, Umblip MW, Siblé DR Moleculopg apd exprespoppertyamine 7 subture. J Biol Chet. 1993; 268: 18200-18204]. Membrane preparations were prepared from cells transfected in this way by homogenizing the cell suspension, followed by separating the plasma membranes from the nuclei, mitochondria, and cell fragments by differential centrifugation. Binding of the studied compounds to the 5-HT 7 receptor was carried out in accordance with the procedure described in [Roth BL, Сraigo SC, Сhoudharu MS, Ulueg S., Monsma FJ, Шеп Y., Меltzer HY, Siblе DR Віpdiпg оf Tourisl Aptuxuсhіturіsl іtcіutіsurіsі agepts to 5-hydrαxytryptami-6-apd 5-hydroxytyptami-7 receptors. J Rhartasol Exp Ther. 1994; 268: 1403-1410]. In a preferred embodiment, cell membranes were incubated with labeled ligand (5.5 nM [ 3 H] LSD) without and in the presence of the test compounds for 2 hours at 25 ° C in an environment consisting of 50 mM Tris-Hcl, pH 7.4, 10 mM MgCl 2 , 0.5 mM EDTA. After incubation, the samples were filtered under vacuum on G / F glass-microfiber filters (Milliro, USA), the filters were washed three times with a cold solution of the medium, and the radioactivity was measured using a MicroBet 340 scintillation counter (RekelPelmer, USA). Non-specific binding, which accounted for 10% of total binding, was determined by incubation of membrane preparations with a radioligand in the presence of 10 μM serotonin.
Связывание тестируемых соединений с рецептором определялось по их способности вытеснять радиоактивный лиганд и выражалось в процентах вытеснения. Процент вытеснения определялся по следующей формуле:  The binding of the test compounds to the receptor was determined by their ability to displace the radioactive ligand and was expressed as a percentage of displacement. The crowding out percentage was determined by the following formula:
%/ = ТА - LCЛA *юo, % / = TA - L C L A * ju,
TA - NA  TA - NA
где ТА - это общая радиоактивность в присутствии только радиоактивного лиганда, CA - это радиоактивность в присутствии радиолиганда и тестируемого соединения и NA - это радиоактивность в присутствии радиолиганда и серотонина (10 μМ). where TA is the total radioactivity in the presence of only a radioactive ligand, CA is radioactivity in the presence of a radioligand and test compound, and NA is radioactivity in the presence of a radioligand and serotonin (10 μM).
Результаты испытаний некоторых представителей соединений общей формулы I, представленные таблице 2, свидетельствуют об активности этих соединений по отношению к серотониновым рецепторам 5-HT7.  The test results of some representatives of the compounds of general formula I, presented in table 2, indicate the activity of these compounds in relation to serotonin receptors 5-HT7.
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ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Таблица 2. Процент вытеснения меченого лиганда LSD, связанного с 5-HT7 рецепторами, под действием 1 мкМ заявляемого вещества. SUBSTITUTE SHEET (RULE 26) Table 2. The percentage of displacement of the labeled LSD ligand associated with 5-HT7 receptors under the action of 1 μm of the claimed substance.
Figure imgf000096_0001
Figure imgf000096_0001
Пример биo-3. Ингибирование бутирилхолинэстеразы. Example bio-3. Inhibition of butyrylcholinesterase.
Результаты испытаний некоторых соединений общей формулы I, представленные в таблице 3, свидетельствуют об ингибирующей активности этих соединений по отношению к бутирилхолинэстеразе BChE.  The test results of some compounds of General formula I, are presented in table 3, indicate the inhibitory activity of these compounds in relation to butyrylcholinesterase BChE.
Таблица 3. Процент ингибирования бутирилхолинэстеразы BChE под действием 1 мкМ заявляемого вещества  Table 3. The percentage inhibition of butyrylcholinesterase BChE under the action of 1 μm of the claimed substance
Figure imgf000096_0002
Figure imgf000096_0002
Пример биo-4. Воздействие заявляемых веществ на митохондрии. Example bio-4. The effect of the claimed substances on mitochondria.
94 94
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Результаты испытаний некоторых соединений общей формулы I, представленные в таблице 4, свидетельствуют об активности этих соединений по отношению к митохондриальным порам MPTP, причем вещества демонстрируют протекторную активность. SUBSTITUTE SHEET (RULE 26) The test results of some compounds of general formula I, presented in table 4, indicate the activity of these compounds in relation to the mitochondrial pores of MPTP, and the substances show protective activity.
Таблица 4. Влияние гидрированных пиpидo[4,3-b] индолов на «нaбyxaниe» митохондрий, трансмембранный потенциал митохондрий и кальциевую ёмкость  Table 4. The effect of hydrogenated pyrido [4,3-b] indoles on mitochondrial “absent”, the transmembrane potential of mitochondria and the calcium capacity
митохонд ий.  mitochondium.
Figure imgf000097_0001
Figure imgf000097_0001
Пример биo-5. Получение фармацевтической композиции. Example bio-5. Obtaining a pharmaceutical composition.
Фармацевтическая композиция согласно изобретению приготавливается с помощью общепринятых в данной области техники приемов и включает фармакологически эффективное количество лекарственной субстанции, представляющей соединение формулы I или его фармацевтически приемлемую соль, составляющей обычно от 5 до 30  The pharmaceutical composition according to the invention is prepared using techniques generally accepted in the art and includes a pharmacologically effective amount of a drug substance representing a compound of formula I or a pharmaceutically acceptable salt thereof, typically from 5 to 30
95  95
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) вec.%, в сочетании с одной или более фармацевтически приемлемыми вспомогательными добавками, такими как стабилизаторы, разбавители, связующие, разрыхляющие агенты, адсорбенты, консерванты, ароматизирующие вещества, вкусовые агенты, красители и т.п.SUBSTITUTE SHEET (RULE 26) wt.%, in combination with one or more pharmaceutically acceptable adjuvants, such as stabilizers, diluents, binders, disintegrating agents, adsorbents, preservatives, flavoring agents, flavoring agents, coloring agents and the like.
В соответствии с известными методами фармацевтические композиции могут быть представлены различными жидкими или твердыми формами. In accordance with known methods, pharmaceutical compositions may be in various liquid or solid forms.
Твердые лекарственные формы включают, например, таблетки, пилюли, желатиновые капсулы и др.  Solid dosage forms include, for example, tablets, pills, gelatine capsules, etc.
Примеры жидких лекарственных форм для инъекций и парентерального введения включают растворы, эмульсии, суспензии и др.  Examples of liquid dosage forms for injection and parenteral administration include solutions, emulsions, suspensions, etc.
Композиции, как правило, получают с помощью стандартных процедур, предусматривающих смешение активного соединения с жидким или тонко измельченным твердым носителем.  Compositions, as a rule, are obtained using standard procedures involving the mixing of the active compound with a liquid or finely divided solid carrier.
Например, 100 мг композиции, содержащей 15.0 мг соединения 649 включает:  For example, 100 mg of a composition containing 15.0 mg of compound 649 includes:
Соединение 649 15.0 мг  Compound 649 15.0 mg
Лактоза 40.0 мг  Lactose 40.0 mg
Альгиновая кислота 20.0 мг  Alginic acid 20.0 mg
Лимонная кислота 5.0 мг  Citric Acid 5.0 mg
Трагакант 20.0 мг  Tragacanth 20.0 mg
Таблетка может быть сформирована посредством прессовки или формовки активного ингредиента с одним или более дополнительными ингредиентами.  A tablet may be formed by compressing or molding the active ingredient with one or more additional ingredients.
Согласно изобретению аналогичным образом получают фармацевтические композиции, содержащие в качестве лекарственной субстанции другие соединения общей формулы I.  According to the invention, pharmaceutical compositions containing other compounds of the general formula I as a drug substance are likewise prepared.
Пример биo-6. Получение лекарственного препарата в форме таблеток.  Example bio-6. Getting the drug in tablet form.
Смешивают 1600 мг крахмала, 1600 мг измельченной лактозы, 400 мг талька и 1000 мг соединения 649 и спрессовывают в брусок. Полученный брусок измельчают в гранулы и просеивают через сита, собирая гранулы размером 14-16 меш. Полученные гранулы таблетируют в подходящую форму таблетки весом 560 мг. 1600 mg of starch, 1600 mg of ground lactose, 400 mg of talc and 1000 mg of compound 649 are mixed and pressed into a block. The resulting bar is crushed into granules and sieved through sieves, collecting granules with a size of 14-16 mesh. The granules obtained are tabletted into a suitable tablet form weighing 560 mg.
Пример биo-7. Получение лекарственного препарата в форме капсул.  Example bio-7. Getting the drug in capsule form.
Тщательно смешивают соединения 649 со следующими ингредиентами: Compound 649 is thoroughly mixed with the following ingredients:
Соединение 649 50.0 мг  Compound 649 50.0 mg
Глицерин 100.0 мг  Glycerin 100.0 mg
Лактоза 290.0 мг  Lactose 290.0 mg
Мятное масло 40.0 мг  Peppermint Oil 40.0 mg
96 96
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) Натрия бензоат 10.0 мг SUBSTITUTE SHEET (RULE 26) Sodium benzoate 10.0 mg
Аскорбиновая кислота 5.0 мг Ascorbic acid 5.0 mg
Тетразин 5.0 мr  Tetrazine 5.0 mr
Полученную порошкообразную смесь упаковывают по 500 мг в желатиновые капсулы подходящего размера. Предлагаемые желатиновые капсулы могут содержать от 1 до 20 % активного ингредиента.  The resulting powder mixture is packaged in 500 mg in a suitable size gelatin capsule. Suggested gelatin capsules may contain from 1 to 20% of the active ingredient.
Пример биo-8. Получение лекарственного препарата В' форме инъекционных композиций для внутримышечных, внутрибрюшинных или подкожных инъекций.  Example bio-8. Preparation of the drug In the form of an injectable composition for intramuscular, intraperitoneal or subcutaneous injection.
Смешивают 500 мг соединения 649 с 300 мг хлорбутанола, 2 мл пропиленгликоля и 100 мл инъекционной воды. Полученный раствор фильтруют и помещают по 1 мл в ампулы, которые стерилизуют и запаивают.  500 mg of compound 649 are mixed with 300 mg of chlorobutanol, 2 ml of propylene glycol and 100 ml of injection water. The resulting solution is filtered and placed in 1 ml ampoules, which are sterilized and sealed.
Согласно изобретению аналогичным образом, в соответствии с примерами биo-6, биo-7 и биo-8, получают лекарственные препараты, содержащие в качестве лекарственной субстанции другие соединения общей формулы I.  According to the invention in a similar manner, in accordance with examples bio-6, bio-7 and bio-8, drugs are prepared containing other compounds of the general formula I as a drug substance.
97 97
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26)  SUBSTITUTE SHEET (RULE 26)

Claims

Производные гидрированных пиpидo[4,3-b] индолов, фармацевтическая композиция, способы получения и применения Формула изобретения Derivatives of hydrogenated pyrido [4,3-b] indoles, pharmaceutical composition, methods for preparing and using the claims
1. Производные гидрированных пиpидo[4,3-b]индoлoв, замещенных в пиперидеиновом фрагменте по положениям 1 и/или 3, в виде оснований или их солей с фармакологически приемлимыми кислотами, а также в виде отдельных оптических изомеров или смесей последних, что в совокупности представлено общей формулой I:  1. Derivatives of hydrogenated pyrido [4,3-b] indoles substituted in the piperidine moiety at positions 1 and / or 3, in the form of bases or their salts with pharmacologically acceptable acids, as well as in the form of individual optical isomers or mixtures of the latter, which in the aggregate is represented by the general formula I:
Figure imgf000100_0001
Figure imgf000100_0001
в которой: wherein:
Z означает необязательно замещенные -(CH2)m-, -(CH2)OiNH-, -(CH2)mO- или - (CH2)mS-; Z is optionally substituted - (CH 2 ) m -, - (CH 2 ) O iNH—, - (CH 2 ) m O— or - (CH 2 ) m S—;
т может принимать значения 2, 3 и 4;  m can take values 2, 3 and 4;
знак (#) здесь и далее обозначает возможность наличия хирального центра;  the sign (#) hereinafter indicates the possibility of a chiral center;
Ar представляет необязательно замещенные арил или гетарил, например, такие, как нафталин, пиридин, пиперидин, индол, бензимидазол, бензоксазол, бензотиазол, индазол, пиримидин, триазин, хинолин, изохинолин, хиназолин, хиноксалин и подобные;  Ar is optionally substituted aryl or hetaryl, for example, such as naphthalene, pyridine, piperidine, indole, benzimidazole, benzoxazole, benzothiazole, indazole, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
Rl представляет H, необязательно замещенный алкил, необязательно замещенный алкокси, галоген, ОН, СFЗ, CN, СFЗО, необязательно замещенную амино-группу, ацильную группу, необязательно замещенный арил или гетарил, алкенил, алкинил, аралкил, алкоксикарбонил, сульфонил, сульфинил, необязательно замещенный аминосульфонил и прочие; Rl также означает возможность наличия аннелированного цикла, например, сформированного такими фрагментами, как метилендиокси, этилен диокси и т.п.;  Rl is H, optionally substituted alkyl, optionally substituted alkoxy, halogen, OH, CF3, CN, CFZO, optionally substituted amino group, acyl group, optionally substituted aryl or hetaryl, alkenyl, alkynyl, aralkyl, alkoxycarbonyl, sulfonyl, sulfinyl, optionally substituted amino-sulfonyl and the like; Rl also means the possibility of the presence of an annelated cycle, for example, formed by fragments such as methylenedioxy, ethylene dioxi, and the like;
R2 представляет H, метил, необязательно замещенные алкил или бензил;  R2 represents H, methyl, optionally substituted alkyl or benzyl;
RЗ и R4 представляют H, метил, необязательно замещенный алкил, или мостик соединяющий положения цикла, состоящий из двух или трех атомов углерода; RЗ и R4 не могут одновременно представлять H: RЗ = R4≠ H.  R3 and R4 are H, methyl, optionally substituted alkyl, or a bridge connecting two or three carbon atoms; R3 and R4 cannot simultaneously represent H: R3 = R4 ≠ H.
98 98
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
2. Соединения по п.l, представляющие производные 2,3,4,5-тeтpaгидpo-l/z- пиpидo[4,3-£]индoлa, замещенные по положениям 1 и/или 3, представленные общими формулами 1-1, 1-2, 1-3, 1-4 и 1-5, 2. Compounds according to claim 1, which are derivatives of 2,3,4,5-tetrahydro-l / z-pyrido [4.3- £] indole substituted at positions 1 and / or 3, represented by general formulas 1-1, 1-2, 1-3, 1-4 and 1-5,
Figure imgf000101_0001
Figure imgf000101_0001
1.1 I.2 1.3 1.1 I.2 1.3
Figure imgf000101_0002
Figure imgf000101_0002
в которых: in which:
Q означает необязательно замещенные группы -CH2CH2- или -CH2CH2O-; Q is optionally substituted —CH 2 CH 2 - or —CH 2 CH 2 O—;
Аlkl представляет метил или этил;  Alkl is methyl or ethyl;
ArI представляет необязательно замещенные фенил или 6-члeнный азагетероцикл, например, такие, как фенил, пиридин, пиперидин, пиримидин, триазин, хинолин, изохинолин, хиназолин, хиноксалин и подобные;  ArI is optionally substituted phenyl or a 6-membered azaheterocycle, for example, such as phenyl, pyridine, piperidine, pyrimidine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline and the like;
Rl и R2 имеют значения, определенные выше.  Rl and R2 are as defined above.
3. Соединения по п.2, включающие следующие стереоизомерно чистые (siпglе isоmеr) подгруппы веществ, представленных общими формулами 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3, 1.3.4, 1.4.1, 1.4.2, 1.5.1 и 1.5.2:  3. The compounds according to claim 2, including the following stereoisomerically pure (sіpglе isomer) subgroup of substances represented by the general formulas 1.1.1, 1.1.2, 1.2.1, 1.2.2, 1.3.1, 1.3.2, 1.3.3 1.3.4, 1.4.1, 1.4.2, 1.5.1 and 1.5.2:
99 99
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
Figure imgf000102_0001
Figure imgf000102_0001
1.1.1 1.1.2 1.2.1 I.2.2  1.1.1 1.1.2 1.2.1 I.2.2
Figure imgf000102_0002
Figure imgf000102_0002
в которых ArI, Rl, R2 и Q имеют значения, определенные выше. in which ArI, Rl, R2, and Q are as defined above.
4. Соединения по любому из пп. 1-3, представляющие:  4. Compounds according to any one of paragraphs. 1-3, representing:
1. l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  1. l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
2. l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индόл  2. l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
3. l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 3. l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
4. l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 4. l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
5. l,3,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3-b]индoл 5. l, 3,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
6. l,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 6. l, 3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
7. l,3,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 7. l, 3,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
8. l,3,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл8. l, 3,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
9. 8-мeтoкcи-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 9. 8-methoxy-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
10.8-мeтoкcи-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 10.8-methoxy-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
11.8-мeтoкcи-l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 11.8-methoxy-l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
12.8-мeтoкcи-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  12.8-methoxy-l, 3-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
13.8-фтop-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 13.8-ftop-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
14.8-фтop-l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл14.8-fluor-l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
15. l,2,3,6-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 15. l, 2,3,6-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
100  one hundred
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
16. 8-xлop-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл16. 8-chlorop-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
17. 8-xлop-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл17. 8-chlorop-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
18. 8-xлop- 1 ,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3-b]индoл18. 8-chloro-1, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
19. 8-xлop-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл19. 8-chlorop-l, 3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
20. 8-бpoм-l,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл20. 8-bromo-l, 3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
21. 8-бpoм-l,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 21. 8-bromo-l, 3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
22. 8-бpoм-l,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 22. 8-bromo-l, 3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
23. 8-бpoм-l,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл23. 8-bromo-l, 3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
24. 8-фтop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл24. 8-fluoro-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
25. 3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 25. 3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
26. 3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  26. 3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
27. 8-xлop- 1 ,2,3-тpимeтил-5-(2-фeнилэтил)-2,3 ,4,5-тeтpaгидpo- 1 H-пиpидo[4,3-b]индoл 27. 8-chloro-1, 2,3-trimethyl-5- (2-phenylethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
28. 3,7,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл28. 3,7,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
29. 3,7,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 29. 3,7,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
30. 3,7,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 30. 3,7,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
31. 3,7,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл31. 3,7,9-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
32. 3,8-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 32. 3,8-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
33. 3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  33. 3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
34. 3,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  34. 3,8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
35. 3,8-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  35. 3,8-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
36. 6-фтop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 36. 6-fluoro-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
37. 3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 37. 3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
38. 3,6-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  38. 3,6-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
39. 6-xлop-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 39. 6-chlorop-l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
40. 8-мeтoкcи-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3-b]индoл40. 8-Methoxy-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
41. 8-мeтoкcи-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 41. 8-methoxy-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
42. 8-мeтoкcи-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 42. 8-methoxy-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
43. 8-мeтoкcи-З -мeтил-5-(2-пиpидин-4-илэтил*)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b] индол43. 8-methoxy-3-methyl-5- (2-pyridin-4-ylethyl * ) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
44. 8-фтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл44. 8-fluoro-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
45. 8-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-4H-пиpидo[4,3-b]индoл 45. 8-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-4H-pyrido [4,3-b] indole
46. 8-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 46. 8-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
47. 8-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл47. 8-fluorop-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
48. 2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 48. 2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
49. 2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  49. 2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
50. 2-бeнзил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  50. 2-benzyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
101 101
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
51. 2,3,7,9-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 51. 2,3,7,9-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
52. 2-этил-3,7,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 52. 2-ethyl-3,7,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
53. 8-бpoм-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 53. 8-bromo-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
54. 2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  54. 2,3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
55. 2-этил-3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  55. 2-ethyl-3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
56. 2-бeнзил-3,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 56. 2-benzyl-3,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
57. 8-этил-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 57. 8-ethyl-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
58. 2,8-диэтил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  58. 2,8-diethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
59. 6-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 59. 6-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
60. 2,3,6,9-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 60. 2,3,6,9-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
61. 2-этил-3,6,9-тpимeтил-5-(2-фeнилэтил)-2,3*,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл61. 2-ethyl-3,6,9-trimethyl-5- (2-phenylethyl) -2,3 * , 4,5-tetrahydro-lH-pyrido [4,3-b] indole
62. 6-xлop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл62. 6-chlorop-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
63. 8-изoпpoпил-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл63. 8-isopropyl-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
64. 6,8-дифтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл64. 6,8-difert-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
65. 6,8-дифтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 65. 6,8-difert-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
66. l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  66. l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
67. 2,3,6-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  67. 2,3,6-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
68. 2-этил-3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  68. 2-ethyl-3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
69. 2-бeнзил-3,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 69. 2-benzyl-3,6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
70. 8-мeтoкcи-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл70. 8-Methoxy-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
71. 2-этил-8-мeтoкcи-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл71. 2-ethyl-8-methoxy-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
72. l,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 72. l, 8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
73. 8-этoкcи-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 73. 8-ethoxy-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
74. l,6-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 74. l, 6-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
75. l,6-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  75. l, 6-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
76. 8-фтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл  76. 8-fluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
77. 2-этил-8-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 77. 2-ethyl-8-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
78. 8-мeтoкcи-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл78. 8-methoxy-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
79. 8-xлop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 79. 8-chlorop-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
80. 8-xлop-2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 80. 8-chlorop-2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
81. 8-мeтoкcи-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл81. 8-methoxy-l-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
82. 8-бpoм-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 82. 8-bromo-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
83. 8-фтop-l-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  83. 8-fluorop-l-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
84. 8-фтop- 1 -мeтил-5 -(2-пиpидин-З -илэтил)-2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -b]индoл 84. 8-fluoro-1-methyl-5 - (2-pyridine-3-ethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
85. 8-фтop-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 85. 8-fluor-l-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
102 102
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
86. 8-xлop-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл86. 8-chlorop-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
87. 8-xлop-l-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 87. 8-chlorop-l-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
88. 6-фтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  88. 6-fluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
89. 2-этил-6-фтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 89. 2-ethyl-6-fluoro-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
90. 8-бpoм-l-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл90. 8-bromo-l-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
91. 6-xлop-2,3 -димeтил-5-(2-фeнилэтил)-2,3 ,4,5 -тетрагидро- 1 H-пиpидo[4,3 -b] индол 91. 6-chlorop-2,3-dimethyl-5- (2-phenylethyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
92. 6-xлop-2-этил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 92. 6-chlorop-2-ethyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
93. 8-бpoм-l-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл93. 8-bromo-l-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
94. 6,8-дифтop-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл94. 6,8-difluoro-2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
95. 2-этил-6,8-дифтop-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл95. 2-ethyl-6,8-difop-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
96. l-мeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол 96. l-methyl-8- (methylcylphonyl) -5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
97. 6-фтop-2,3,9-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 97. 6-fluoro-2,3,9-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
98. 2-этил-6-фтop-3,9-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeτpaгидpo-Ш-пиpидo[4,3-b]индoл98. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
99. 1 ,2-димeтил-5 -(2-фeнилэтил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b] индол 99. 1, 2-dimethyl-5 - (2-phenylethyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
100. l,2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 100. l, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
101. l,2,6-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл101. l, 2,6-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
102. 8-мeтoкcи-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 102. 8-methoxy-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
103. 8-фтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 103. 8-fluoro-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
104. 8-xлop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл104. 8-chlorop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
105. 6-фтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл105. 6-fluorop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
106. 6-xлop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл106. 6-chlorop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
107. 6,8-дифтop-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 107. 6,8-diptop-l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
108. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  108. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-phenylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
109. 12-мeтил-5-(2-фeнилэтил)-6,7,8,9, 10,11 -гeкcaгидpo-5H-7, 11 - эпиминоциклооктаfb] индол  109. 12-methyl-5- (2-phenylethyl) -6,7,8,9, 10,11-hexahydro-5H-7, 11 - epiminocyclocta fb] indole
110. 2,12-димeтил-5-(2-фeнилэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  110. 2,12-dimethyl-5- (2-phenylethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
111. 1 l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  111. 1 l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
112. 2,1 l-димeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  112. 2,1 l-dimethyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
103 103
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
113. 2-мeтoкcи-l 1 -мeтил-5-(2-фeнилэтил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл 113. 2-methoxy-l 1-methyl-5- (2-phenylethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
114. 2-фтop-l l-мeтил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  114. 2-ftop-l l-methyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [b] indole
115. 2-xлop-l 1 -мeтил-5-(2-фeнилэтил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  115. 2-chlorop-l 1-methyl-5- (2-phenylethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
116. l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  116. l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
117. l,2,3,8-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2»3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 117. l, 2,3,8-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2 ” 3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
118. l,2,3,6-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  118. l, 2,3,6-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
119. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  119. 8-methoxy-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
120. 8-фтop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  120. 8-fluor-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
121. 8-xлop-l ,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  121. 8-chlorop-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
122. 6-фтop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  122. 6-fluoro-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
123. 6-xлop-l,2,3-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  123. 6-chlorop-l, 2,3-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
124. 2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 124. 2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
125. 2-этил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 125. 2-ethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
126. 2,3,7,9-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  126. 2,3,7,9-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
127. 2-этил-3,7,9-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  127. 2-ethyl-3,7,9-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
128. 2,3,8-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4^-тeтpaгидpo-lH-пиpидo[4,3- b] индол  128. 2,3,8-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4 ^ -tetrahydro-lH-pyrido [4,3-b] indole
129. 2-этил-3,8-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  129. 2-ethyl-3,8-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
130. 8-этил-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  130. 8-ethyl-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
104 104
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
131. 2,8-диэтил-3-мeтил-5-[2-(4-мeтилфeнил)эτил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 131. 2,8-diethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
132. 2,3,6,9-тeтpaмeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  132. 2,3,6,9-tetramethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
133. 2-этил-3,6,9-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  133. 2-ethyl-3,6,9-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
134. 2,3,6-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  134. 2,3,6-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
135. 2-этил-3,6-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  135. 2-ethyl-3,6-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
136. 8-мeтoкcи-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  136. 8-methoxy-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
137. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-bjиндол  137. 2-ethyl-8-methoxy-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
138. 8-этoкcи-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  138. 8-ethoxy-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
139. 8-фтop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  139. 8-fluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
140. 2-этил-8-фтop-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-lH- пиpидo[4,3-b]индoл  140. 2-ethyl-8-fluoro-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
141. 8-xлop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  141. 8-chlorop-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
142. 8-xлop-2-этил-3 -мeтил-5 - [2-(4-мeтилфeнил)этия]-2,3 ,4,5-тeтpaгидpo- 1 H- пиридо [4,3 -b]индoл  142. 8-chlorop-2-ethyl-3-methyl-5 - [2- (4-methylphenyl) ethium] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
143. 6-фтop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  143. 6-fluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
144. 2-этил-6-фтop-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пири до [4, 3 -b] индол  144. 2-ethyl-6-fluoro-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Shpiri to [4, 3-b] indole
145. 6-xлop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  145. 6-chlorop-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
146. 6-xлop-2-этил-3-мeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b] индол  146. 6-chlorop-2-ethyl-3-methyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
147. 6,8-дифтop-2,3-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  147. 6,8-difluoro-2,3-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
105 105
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
148. 2-этил-6,8-дифтop-3 -мeтил-5 - [2-(4-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиpидo[4,3-b]индoл 148. 2-ethyl-6,8-difop-3-methyl-5 - [2- (4-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
149. 6-фтop-2,3,9-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  149. 6-fluoro-2,3,9-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
150. 2-этил-6-фтop-3,9-димeтил-5-[2-(4-мeтилфeнил}этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  150. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (4-methylphenyl} ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
151. l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 151. l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
152. l,2,8-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 152. l, 2,8-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
153. 8-этил-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  153. 8-ethyl-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
154. l,2,6-тpимeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  154. l, 2,6-trimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
155. 8-мeтoкcи- 1 ,2-димeтил-5 - [2-(4-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиpидo[4,3-b]индoл  155. 8-methoxy-1, 2-dimethyl-5 - [2- (4-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
156. 8-этoкcи-l,2-димeтил-5-[2-(4-мeтилфeнил)этил^-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  156. 8-ethoxy-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl ^ -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
157. 8-фтop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  157. 8-fluorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
158. 8-xлop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  158. 8-chlorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
159. 6-фтop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  159. 6-fluoro-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
160. 6-xлop-l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  160. 6-chlorop-l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
161. 6,8-дифтop-l,2-димeтил-5-[2-(4-мeтилфeнил)эт,ил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  161. 6,8-diflurop-l, 2-dimethyl-5- [2- (4-methylphenyl) et, yl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
162. l,2-димeтил-5-[2-(4-мeтилфeнил)этил]-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  162. l, 2-dimethyl-5- [2- (4-methylphenyl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
163. 12-мeтил-5-[2-(4-мeтилфeнил)этил]-6,7, 8,9,10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  163. 12-methyl-5- [2- (4-methylphenyl) ethyl] -6,7, 8,9,10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
164. 2,12-димeтил-5-[2-(4-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  164. 2,12-dimethyl-5- [2- (4-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
165. l l-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  165. l l-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
106 106
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
166. 2,11 -димeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол 166. 2,11-dimethyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
167. 2-мeтoкcи-l l-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  167. 2-methoxy-l l-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
168. 2-фтop-l l-мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  168. 2-fluorop-l-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
169. 2-xлop-l 1 -мeтил-5-[2-(4-мeтилфeнил)этил]-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  169. 2-chlorop-l 1-methyl-5- [2- (4-methylphenyl) ethyl] -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
170. l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,475-тeтpaгидpo-lH-пиpидo[4,3- b] индол  170. l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,475-tetrahydro-lH-pyrido [4,3-b] indole
171. 1 ,2,3,8-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo- 1 H-пиpидo[4,3- b] индол  171. 1, 2,3,8-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
172. l,2,3,6-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  172. l, 2,3,6-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
173. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  173. 8-methoxy-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
174. 8-фтop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш- пиридо [4,3 -b]индoл  174. 8-fluorop-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
175. 8-xлop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  175. 8-chlorop-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
176. 6-фтop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  176. 6-fluoro-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
177. 6-xлop-l,2,3-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  177. 6-chlorop-l, 2,3-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
178. 2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 178. 2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
179. 2,3,7,9-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 179. 2,3,7,9-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
180. 2-этил-3,7,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  180. 2-ethyl-3,7,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
181. 2,3,8-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,475-тeтpaгидpo-lH-пиpидo[4,3- b]индол  181. 2,3,8-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,475-tetrahydro-lH-pyrido [4,3-b] indole
182. 2-этил-3,8-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  182. 2-ethyl-3,8-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
183. 8-этил-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  183. 8-ethyl-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
107 107
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
184. 2,8-диэтил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 184. 2,8-diethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
185. 2,3,6,9-тeтpaмeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  185. 2,3,6,9-tetramethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
186. 2-этил-3,6,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  186. 2-ethyl-3,6,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
187. 2,3,6-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  187. 2,3,6-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
188. 2-этил-3 ,6-димeтил-5 - [2-(2-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  188. 2-ethyl-3, 6-dimethyl-5 - [2- (2-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
189. 8-мeтoкcи-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  189. 8-methoxy-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
190. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5*гeтparидpo-Ш- пиридо [4,3 -bjиндол  190. 2-ethyl-8-methoxy-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5 * getparidro-Sh-pyrido [4,3-bjindole
191. 8-этoкcи-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  191. 8-ethoxy-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
192. 8-фтop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  192. 8-fluoro-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
193. 2-этил-8-фтop-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  193. 2-ethyl-8-fluoro-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
194. 8-xлop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  194. 8-chlorop-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
195. 8-xлop-2-этил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  195. 8-chlorop-2-ethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
196. 6-фтop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  196. 6-fluoro-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
197. 2-этил-6-фтop-3 -мeтил-5-[2-(2-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -bjиндол  197. 2-ethyl-6-fluoro-3-methyl-5- [2- (2-methylphenyl) ethyl] -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-bjindole
198. 6-xлop-2,3-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  198. 6-chlorop-2,3-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
199. 6-xлop-2-этил-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  199. 6-chlorop-2-ethyl-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
200. 6,8-дифтop-2,3-димeтил-5-[2-(2-мeтилфeнил)эΗϊл]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл »  200. 6,8-difluoro-2,3-dimethyl-5- [2- (2-methylphenyl) en] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole "
108 108
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
201. 2-этил-6,8-дифтop-3-мeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш- пиридо [4 ,3 -b] индол 201. 2-ethyl-6,8-difop-3-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetra-para-Sh-pyrido [4, 3-b] indole
202. 6-фтop-2,3,9-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  202. 6-fluoro-2,3,9-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
203. 2-этил-6-фтop-3,9-димeтил-5-[2-(2-мeтилфeнид)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл ^ 203. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (2-methylphenide) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole ^
204. l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 204. l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
205. l,2,8-тpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 205. l, 2,8-trimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
206. 8-этил-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  206. 8-ethyl-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
207. l,2,6-τpимeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  207. l, 2,6-τ-methyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
208. 8-мeтoкcи- 1 ,2-димeтил-5- [2-(2-мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -b]индoл  208. 8-methoxy-1, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
209. 8-фтop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  209. 8-fluorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
210. 8-xлop- 1 ,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3 ,4,5-тeтpaгидpo- 1 H-пиpидo[4,3- b] индол  210. 8-chloro-1, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
211. 6-фтop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  211. 6-fluorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
212. 6-xлop-l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  212. 6-chlorop-l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
213. 6,8-дифтop-l,2-димeтил-5-[2-(2-мeти"лфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  213. 6,8-diptop-l, 2-dimethyl-5- [2- (2-meti "lphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
214. l,2-димeтил-5-[2-(2-мeтилфeнил)этил]-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  214. l, 2-dimethyl-5- [2- (2-methylphenyl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
215. 12-мeтил-5-[2-(2-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  215. 12-methyl-5- [2- (2-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
216. 2,12-димeтил-5-[2-(2-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминоциклооктаfb] индол  216. 2,12-dimethyl-5- [2- (2-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclocta fb] indole
217. l l-мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  217. l l-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
218. 2,11 -димeтил-5-[2-(2-мeтилфeнил)этил]-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  218. 2,11-dimethyl-5- [2- (2-methylphenyl) ethyl] -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
109 109
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
219. 2-мeтoкcи- 11 -мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9, 10-reкcarидpo-7, 10- эпиминoциклoгeптa[b] индол 219. 2-methoxy-11-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9, 10-recarcidro-7, 10-epiminocyclohepta [b] indole
220. 2-фтop-l l-мeтил-5-[2-(2-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  220. 2-fluorop-l l-methyl-5- [2- (2-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
221. 2-xлop- 11 -мeтил-5-[2-(2-мeтилфeнил)этил]-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  221. 2-chloro-11-methyl-5- [2- (2-methylphenyl) ethyl] -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
222. 1 ,2,3 -тpимeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  222. 1, 2,3 -trimethyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
223. l,2,3,8-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  223. l, 2,3,8-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
224. l,2,3,6-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  224. l, 2,3,6-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
225. 8-мeтoкcи-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  225. 8-methoxy-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
226. 8-фтop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  226. 8-fluor-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
227. 8-xлop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  227. 8-chlorop-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
228. 6-фтop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  228. 6-fluoro-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
229. 6-xлop-l,2,3-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  229. 6-chlorop-l, 2,3-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
230. 2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 230. 2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
231. 2-этил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 231. 2-ethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
232. 2,3,7,9-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  232. 2,3,7,9-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
233. 2-этил-3,7,9-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-lH- пиpидo[4,3-b]индoл  233. 2-ethyl-3,7,9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetraparidro-lH-pyrido [4,3-b] indole
234. 2,3,8-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  234. 2,3,8-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
235. 2-этил-3,8-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  235. 2-ethyl-3,8-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
236. 8-этил-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  236. 8-ethyl-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
ПО ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) BY SUBSTITUTE SHEET (RULE 26)
237. 2,8-диэтил-3-мeтил-5-[2-(3-мeтилфeцил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 237. 2,8-diethyl-3-methyl-5- [2- (3-methyl-phenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
238. 2,3,6,9-тeтpaмeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  238. 2,3,6,9-tetramethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
239. 2-этил-3,6,9-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  239. 2-ethyl-3,6,9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
240. 2,3,6-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  240. 2,3,6-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
241. 2-этил-3,6-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  241. 2-ethyl-3,6-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
242. 8-мeтoкcи-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  242. 8-methoxy-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
243. 2-этил-8-мeтoкcи-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  243. 2-ethyl-8-methoxy-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
244. 8-этoкcи-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-1H- пиpидo[4,3-b]индол  244. 8-ethoxy-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole
245. 8-фтop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  245. 8-fluoro-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
246. 2-этил-8-фтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  246. 2-ethyl-8-fluoro-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
247. 8-xлop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  247. 8-chlorop-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
248. 8-xлop-2-этил-3 -мeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5 -тетраrидро- 1 H- пиридо [4,3 -b] индол  248. 8-chlorop-2-ethyl-3-methyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
249. 6-фтop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  249. 6-fluoro-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
250. 2-этил-6-фтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  250. 2-ethyl-6-fluoro-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
251. 6-xлop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  251. 6-chlorop-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
252. 6-xлop-2-этил-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  252. 6-chlorop-2-ethyl-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
253. 6,8-дифтop-2,3-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  253. 6,8-difluoro-2,3-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
111 111
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
254. 2-этил-6,8-дифтop-3-мeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл 254. 2-ethyl-6,8-difop-3-methyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
255. 6-фтop-2,3 ,9-тpимeтил-5- [2-(3 -мeтилфeнил)этил] -2,3 ,4,5-тeтpaгидpo- 1 H- пири до [4 , 3 -b] индол  255. 6-fluoro-2,3, 9-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyri to [4, 3-b] indole
256. 2-этил-6-фтop-3,9-димeтил-5-[2-(3-мέтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  256. 2-ethyl-6-fluoro-3,9-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
257. l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 257. l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
258. 1 ,2,8-тpимeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол 258. 1, 2,8-trimethyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
259. 8-этил-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  259. 8-ethyl-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
260. l,2,6-тpимeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  260. l, 2,6-trimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
261. 8-мeтoкcи- 1 ,2-димeтил-5 - [2-(3 -мeтилфeнил)этил]-2,3 ,4,5-тeтpaгидpo- 1 H- пиpидo[4,3-b]индoл  261. 8-methoxy-1, 2-dimethyl-5 - [2- (3-methylphenyl) ethyl] -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
262. 8-этoкcи-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пири д о [4 , 3 -b] индол  262. 8-ethoxy-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyro d [4, 3-b] indole
263. 8-фтop- 1 ,2-димeтил-5 - [2-(3 -мeтилфeнил)этил] -2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - bjиндол  263. 8-ftop-1, 2-dimethyl-5 - [2- (3-methylphenyl) ethyl] -2.3, 4,5-tetrahydro-1 H-pyrido [4,3 - bjindole
264. 8-xлop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  264. 8-chlorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
265. 6-фтop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b] индол  265. 6-fluorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
266. 6-xлop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  266. 6-chlorop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
267. 6,8-дифтop-l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  267. 6,8-diptop-l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
268. l,2-димeтил-5-[2-(3-мeтилфeнил)этил]-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4 , 3 -b] индол  268. l, 2-dimethyl-5- [2- (3-methylphenyl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-1 H-pyrido [4, 3-b] indole
269. 12-мeтил-5-[2-(3-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  269. 12-methyl-5- [2- (3-methylphenyl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
270. 2,12-димeтил-5-[2-(3-мeтилфeнил)этил]-6,7,8,9,10,l l-гeкcarидpo-5H-7,l 1- эпиминoциклooктa[b] индол  270. 2,12-dimethyl-5- [2- (3-methylphenyl) ethyl] -6,7,8,9,10, l l-hexcaridro-5H-7, l 1-epiminocyclooct [b] indole
271. 11 -мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  271. 11-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
112 112
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
272. 2,l l-димeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол 272. 2, l l-dimethyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
273. 2-мeтoкcи- 11 -мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  273. 2-methoxy-11-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
274. 2-фтop-l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  274. 2-fluorop-l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
275. 2-xлop-l l-мeтил-5-[2-(3-мeтилфeнил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  275. 2-chlorop-l l-methyl-5- [2- (3-methylphenyl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
276. 5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  276. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
277. 5-[2-(4-фтopфeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  277. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
278. 5-[2-(4-фтopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  278. 5- [2- (4-fluorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
279. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  279. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
280. 8-фтop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  280. 8-fluorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
281. 8-xлop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  281. 8-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
282. 6-фтop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3 -b] индол  282. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
283. 6-xлop-5-[2-(4-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  283. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
284. 5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 284. 5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
285. 2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 285. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
286. 5-[2-(4-фтopфeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  286. 5- [2- (4-fluorophenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
287. 2-этил-5-[2-(4-фтopфeнил)этил]-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  287. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,7,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
288. 5-[2-(4-фтopфeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-.lH-пиpидo[4,3- b] индол  288. 5- [2- (4-fluorophenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-.lH-pyrido [4,3-b] indole
289. 2-этил-5-[2-(4-фтopфeнил)этил]-3,8-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  289. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,8-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
ИЗOF
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
290. 8-этил-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 290. 8-ethyl-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
291. 2,8-диэтил-5-[2-(4-фтopфeнил)этил]-3-мeтил-23,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  291. 2,8-diethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-23,4,5-tetrahydro-III-pyrido [4,3-b] indole
292. 5- [2-(4-фтopфeнил)этил] -2,3 ,6,9-тeтpaмeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3- b] индол  292. 5- [2- (4-fluorophenyl) ethyl] -2,3, 6,9-tetramethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
293. 2-этил-5-[2-(4-фтopфeнил)этил]-3,6,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  293. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3,6,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
294. 5-[2-(4-фтopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  294. 5- [2- (4-fluorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
295. 2-этил-5 - [2-(4-фтopфeнил)этил] -3 ,6-димeтил-2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол  295. 2-ethyl-5 - [2- (4-fluorophenyl) ethyl] -3, 6-dimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
296. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  296. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
297. 2-этил-5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  297. 2-ethyl-5- [2- (4-fluorophenyl) ethyl] -8-methoxy-3-methyl-2,3,4,5-tetrahydro-Ш-pyrido [4, 3-b] indole
298. 8-этoкcи-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  298. 8-ethoxy-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
299. 8-фтop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  299. 8-fluorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
300. 2-этил-8-фтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  300. 2-ethyl-8-fluorop-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
301. 8-xлop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  301. 8-chlorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
302. 8-xлop-2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтp.aгидpo-Ш- пиридо [4,3 -b] индол  302. 8-chlorop-2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
303. 6-фтop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  303. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
304. 2-этил-6-фтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  304. 2-ethyl-6-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
305. 6-xлop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  305. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
306. 6-xлop-2-этил-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b]индoл  306. 6-chlorop-2-ethyl-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
114 114
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
307. 6,8-дифтop-5-[2-(4-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл 307. 6,8-diptop-5- [2- (4-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
308. 2-этил-6,8-дифтop-5-[2-(4-фтopфeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  308. 2-ethyl-6,8-difop-5- [2- (4-fluorophenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
309. 6-фтop-5-[2-(4-фтopфeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  309. 6-fluorop-5- [2- (4-fluorophenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
310. 2-этил-6-фтop-5-[2-(4-фтopфeнил)этил]-3,9-димeтил-2,3,4,5-тeтparидpo-Ш- пиридо[4,3-b]индол  310. 2-ethyl-6-fluorop-5- [2- (4-fluorophenyl) ethyl] -3,9-dimethyl-2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
311. 5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 311. 5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
312. 5-[2-(4-фтopфeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 312. 5- [2- (4-fluorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
313. 8-этил-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  313. 8-ethyl-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
314. 5-[2-(4-фтopфeнил)этил]-l,2,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  314. 5- [2- (4-fluorophenyl) ethyl] -l, 2,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
315. 5-[2-(4-фтopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  315. 5- [2- (4-fluorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
316. 8-этoкcи-5-[2-(4-фтopфeнил)этил]-1,2-димeтил-2,3,4,5-тeтpaгидpo-1H-пиpидo[4,3- b]индол  316. 8-ethoxy-5- [2- (4-fluorophenyl) ethyl] -1,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole
317. 8-фтop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  317. 8-fluorop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
318. 8-xлop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  318. 8-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
319. 6-фтop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  319. 6-fluoro-5- [2- (4-fluoro-phenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
320. 6-xлop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  320. 6-chlorop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
321. 6,8-дифтop-5-[2-(4-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  321. 6,8-diptop-5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
322. 5-[2-(4-фтopфeнил)этил]-l,2-димeтил-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-bjиндол  322. 5- [2- (4-fluorophenyl) ethyl] -l, 2-dimethyl-8- (methylcylphonyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
323. 5-[2-(4-фтopфeнил)этил]-12-мeтил-6,7,8,9,10,ll-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  323. 5- [2- (4-fluorophenyl) ethyl] -12-methyl-6,7,8,9,10, ll-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
324. 5-[2-(4-фтopфeнил)этил]-2,12-димeтил-6,7,8,9,10,1l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  324. 5- [2- (4-fluorophenyl) ethyl] -2,12-dimethyl-6,7,8,9,10,1l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
115 115
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
325. 5-[2-(4-фтopфeнил)этил]- 11 -мeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол 325. 5- [2- (4-fluorophenyl) ethyl] - 11-methyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
326. 5-[2-(4-фтopфeнил)этил]-2, 11 -димeтил-5,6, 7,8,9, 10-reкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  326. 5- [2- (4-fluorophenyl) ethyl] -2, 11-dimethyl-5,6, 7,8,9, 10-rehydro-7, 10-epiminocyclohepta [b] indole
327. 5-[2-(4-фтopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  327. 5- [2- (4-fluorophenyl) ethyl] -2-methoxy-l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
328. 2-фтop-5-[2-(4-фтopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  328. 2-fluorop-5- [2- (4-fluorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
329. 2-xлop-5-[2-(4-фтopфeнил)этил]- 11 -мeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  329. 2-chlorop-5- [2- (4-fluorophenyl) ethyl] - 11-methyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
330. 5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  330. 5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
331. 5 -[2-(4-xлopфeнил)этил] - 1 ,2,3 ,8-тeтpaмeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  331. 5 - [2- (4-chlorophenyl) ethyl] - 1, 2,3, 8-tetramethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
332. 5-[2-(4-xлopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  332. 5- [2- (4-chlorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
333. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  333. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
334. 5-[2-(4-xлopфeнил)этил]-8-фтop-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  334. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
335. 8-xлop-5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  335. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
336. 5-[2-(4-xлopфeнил)этил]-6-фтop-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  336. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
337. 6-xлop-5-[2-(4-xлopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  337. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
338. 5- [2-(4-xлopфeнил)этил] -2,3 -димeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b]индoл 338. 5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
339. 5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 339. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
340. 5-[2-(4-xлopфeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  340. 5- [2- (4-chlorophenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
341. 5-[2-(4-xлopфeнил)этил]-2-этил-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  341. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,7,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
342. 5-[2-(4-xлopфeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  342. 5- [2- (4-chlorophenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
116 116
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
343. 5 - [2-(4-xлopфeнил)этил] -2-этил-3 ,8-димeтил-2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол 343. 5 - [2- (4-chlorophenyl) ethyl] -2-ethyl-3, 8-dimethyl-2,3, 4,5-tetrahydro- 1 N-pyrido [4,3 - b] indole
344. 5-[2-(4-xлopфeнил)этил]-8-этил-2,3-димeтил-2,"3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 344. 5- [2- (4-chlorophenyl) ethyl] -8-ethyl-2,3-dimethyl-2, " 3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
345. 5-[2-(4-xлopфeнил)этил]-2,8-диэтил-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  345. 5- [2- (4-chlorophenyl) ethyl] -2,8-diethyl-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
346. 5 - [2-(4-xлopфeнил)этил] -2,3 ,6,9-тeтpaмeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  346. 5 - [2- (4-chlorophenyl) ethyl] -2,3, 6,9-tetramethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
347. 5-[2-(4-xлopфeнил)этил]-2-этил-3,6,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  347. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,6,9-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
348. 5-[2-(4-xлopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  348. 5- [2- (4-chlorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
349. 5-[2-(4-xлopфeнил)этил]-2-этил-3,6-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  349. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3,6-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
350. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 , 3 -b] индол  350. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
351. 5-[2-(4-xлopфeнил)этил]-2-этил-8-мeтoкcи-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  351. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-8-methoxy-3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
352. 5-[2-(4-xлopфeнил)этил]-8-фтop-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  352. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
353. 5-[2-(4-xлopфeнил)этил]-2-этил-8-фтop-3-мeтил-2,3,4,5-тeтparидpo-Ш- пиpидo[4,3 -b] индол  353. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-8-fluoro-3-methyl-2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
354. 8-xлop-5- [2-(4-xлopфeнил)этил] -2,3 -димeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  354. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
355. 8-xлop-5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  355. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
356. 5-[2-(4-xлopфeнил)этил]-6-фтop-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  356. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
357. 5 - [2-(4-xлopфeнил)этил] -2-этил-6-фтop-3 -мeтил-2,3 ,4,5-тeтpaгидpo- 1 H- пиpидo[4,3 -b] индол  357. 5 - [2- (4-chlorophenyl) ethyl] -2-ethyl-6-fluoro-3-methyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
358. 6-xлop-5-[2-(4-xлopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  358. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
359. 6-xлop-5-[2-(4-xлopфeнил)этил]-2-этил-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  359. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -2-ethyl-3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
117 117
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
360. 5-[2-(4-xлopфeнил)этил]-6,8-дифтop-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол 360. 5- [2- (4-chlorophenyl) ethyl] -6,8-difluoro-2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
361. 5-[2-(4-xлopфeнил)этил]-2-этил-6,8-дифтop-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  361. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-6,8-difluoro-3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
362. 5-[2-(4-xлopфeнил)этил]-6-фтop-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  362. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-2,3,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
363. 5-[2-(4-xлopфeнил)этил]-2-этил-6-фтop-3,9-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  363. 5- [2- (4-chlorophenyl) ethyl] -2-ethyl-6-fluoro-3,9-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
364. 5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 364. 5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
365. 5-[2-(4-xлopфeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 365. 5- [2- (4-chlorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
366. 5-[2-(4-xлopфeнил)этил]-8-этил-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  366. 5- [2- (4-chlorophenyl) ethyl] -8-ethyl-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
367. 5-[2-(4-xлopфeнил)этил]-l,2,6-тpимejил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  367. 5- [2- (4-chlorophenyl) ethyl] -l, 2,6-trimimel-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
368. 5-[2-(4-xлopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  368. 5- [2- (4-chlorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
369. 5-[2-(4-xлopфeнил)этил]-8-фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  369. 5- [2- (4-chlorophenyl) ethyl] -8-fluoro-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
370. 8-xлop-5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  370. 8-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
371. 5-[2-(4-xлopфeнил)этил]-6-фтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  371. 5- [2- (4-chlorophenyl) ethyl] -6-fluoro-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
372. 6-xлop-5-[2-(4-xлopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  372. 6-chlorop-5- [2- (4-chlorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
373. 5-[2-(4-xлopфeнил)этил]-6,8-дифтop-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  373. 5- [2- (4-chlorophenyl) ethyl] -6,8-diflt-l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
374. 5-[2-(4-xлopфeнил)этил]-12-мeтил-6,7,8,9,10,ll-гeкcaгидpo-§H-7,l 1- эпиминoциклooктa[b]индoл  374. 5- [2- (4-chlorophenyl) ethyl] -12-methyl-6,7,8,9,10, ll-hexahydro-§H-7, l 1-epiminocyclooct [b] indole
375. 5-[2-(4-xлopфeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  375. 5- [2- (4-chlorophenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
376. 5-[2-(4-xлopфeнил)этил]-ll-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индол  376. 5- [2- (4-chlorophenyl) ethyl] -ll-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
377. 5-[2-(4-xлopфeнил)этил]-2,ll-димeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индол  377. 5- [2- (4-chlorophenyl) ethyl] -2, ll-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
118 118
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
378. 5-[2-(4-xлopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол 378. 5- [2- (4-chlorophenyl) ethyl] -2-methoxy-l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
379. 5-[2-(4-xлopфeнил)этил]-2-фтop-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  379. 5- [2- (4-chlorophenyl) ethyl] -2-ftop-l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
380. 2-xлop-5-[2-(4-xлopфeнил)этил]-l l-мeтил-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциicлoгeптa[b]индoл  380. 2-chlorop-5- [2- (4-chlorophenyl) ethyl] -l l-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohept [b] indole
381. 5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  381. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
382. 5-[2-(4-мeтoкcифeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-bjиндол  382. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
383. 5-[2-(4-мeтoкcифeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaтидpo-lH- пиридо[4,3-bjиндол  383. 5- [2- (4-Methoxyphenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetratidro-lH-pyrido [4,3-bjindole
384. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  384. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
385. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  385. 8-fluorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
386. 8-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтparидpo-Ш- пиpидo[4,3-b]индол  386. 8-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetra-para-III-pyrido [4,3-b] indole
387. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  387. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
388. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  388. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
389. 5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  389. 5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
390. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  390. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
391. 5-[2-(4-мeтoкcифeнил)этил]-2,3,7,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  391. 5- [2- (4-methoxyphenyl) ethyl] -2,3,7,9-tetramethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
392. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,7,9-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индол  392. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,7,9-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
393. 5-[2-(4-мeтoкcифeнил)этил]-2,3,8-тpимeтил-2,J,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  393. 5- [2- (4-methoxyphenyl) ethyl] -2,3,8-trimethyl-2, J, 4,5-tetrahydro-III-pyrido [4,3-b] indole
394. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,8-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  394. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,8-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
119 119
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
395. 8-этил-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл 395. 8-ethyl-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
396. 2,8-диэтил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индо л  396. 2,8-diethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indo l
397. 5-[2-(4-мeтoкcифeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  397. 5- [2- (4-methoxyphenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
398. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3,6,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  398. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3,6,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
399. 5-[2-(4-мeтoкcифeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  399. 5- [2- (4-methoxyphenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
400. 2-этил-5-[2-(4-мeтoкcифeнил)этил]-3*,6-димeтил-2,3,4,5-тeтpaгидpo-1H- пиридо[4,3-b]индол  400. 2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3 *, 6-dimethyl-2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole
401. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтparидpo-lH- пиридо[4,3-b]индол  401. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
402. 2-этил-8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  402. 2-ethyl-8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Ш-pyrido [4,3-b] indole
403. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индол  403. 8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
404. 2-этил-8-фтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  404. 2-ethyl-8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
405. 8-xлop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  405. 8-chlorop-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
406. 8-xлop-2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  406. 8-chlorop-2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
407. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  407. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
408. 2-этил-6-фтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  408. 2-ethyl-6-fluorop-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
409. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  409. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
410. 6-xлop-2-этил-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  410. 6-chlorop-2-ethyl-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
411. 6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  411. 6,8-difert-5- [2- (4-methoxyphenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
120 120
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
412. 2-этил-6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-3-мeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол 412. 2-ethyl-6,8-difop-5- [2- (4-methoxyphenyl) ethyl] -3-methyl-2,3,4,5-tetrahydro-Ш-pyrido [4,3 -b] indole
413. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  413. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
414. 2-этил-6-фтop-5-[2-(4-мeтoкcифeнил)этил]-3,9-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  414. 2-ethyl-6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -3,9-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
415. 5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo*lH-rшpидo[4,3- b] индол  415. 5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro * lH-r-shredo [4,3-b] indole
416. 5-[2-(4-мeтoкcифeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  416. 5- [2- (4-methoxyphenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
417. 8-этил-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4 ,3 -b] индол  417. 8-ethyl-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
418. 5 - [2-(4-мeтoкcифeнил)этил] - 1 ,2,6-тpимeтил-2,3 ,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 - b] индол  418. 5 - [2- (4-methoxyphenyl) ethyl] - 1, 2,6-trimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
419. 8-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  419. 8-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
420. 8-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  420. 8-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
421. 8 -xлop-5 - [2-(4-мeтoкcифeнил)этил] - 1 ,2- димeтил-2 ,3 ,4, 5 -тетраги дро- IH- пиридо [4, 3 -b] индол  421. 8-chloro-5 - [2- (4-methoxyphenyl) ethyl] - 1, 2-dimethyl-2, 3, 4, 5-tetra-dro-IH-pyrido [4, 3-b] indole
422. 6-фтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  422. 6-fluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
423. 6-xлop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  423. 6-chlorop-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
424. 6,8-дифтop-5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  424. 6,8-difluoro-5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
425. 5-[2-(4-мeтoкcифeнил)этил]-l,2-димeтил-8-(мetилcyльфoнил)-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  425. 5- [2- (4-methoxyphenyl) ethyl] -l, 2-dimethyl-8- (methylcyclonyl) -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
426. 5-[2-(4-мeтoкcифeнил)этил]-12-мeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  426. 5- [2- (4-methoxyphenyl) ethyl] -12-methyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
427. 5-[2-(4-мeтoкcифeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  427. 5- [2- (4-methoxyphenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
428. 5-[2-(4-мeтoкcифeнил)этил] - 11 -мeтил-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  428. 5- [2- (4-methoxyphenyl) ethyl] - 11-methyl-5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
121 121
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
429. 5-[2-(4-мeтoкcифeнил)этил]-2, 11 -димeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл 429. 5- [2- (4-methoxyphenyl) ethyl] -2, 11-dimethyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
430. 2-мeтoкcи-5-[2-(4-мeтoкcифeнил)этил]-l l-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  430. 2-methoxy-5- [2- (4-methoxyphenyl) ethyl] -l l-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
431. 2-фтop-5-[2-(4-мeтoкcифeнил)этил]- 11 -мeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  431. 2-fluorop-5- [2- (4-methoxyphenyl) ethyl] - 11-methyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
432. 2-xлop-5-[2-(4-мeтoкcифeнил)этил]- JД-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  432. 2-chlorop-5- [2- (4-methoxyphenyl) ethyl] - J-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
433. 1 ,2,3 -тpимeтил-5 - { 2- [4-(тpифтopмeтил)фeнил] этил } -2,3 ,4,5-тeтpaгидpo- 1 H- пиридо [4,3 -b]индoл  433. 1, 2,3-trimethyl-5 - {2- [4- (triflumethyl) phenyl] ethyl} -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b] indole
434. l,2,3,8-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  434. l, 2,3,8-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
435. l,2,3,6-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  435. l, 2,3,6-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
436. 8-фтop- 1 ,2,3 -тpимeтил-5 - { 2- [4-(тpифтopмeтил)фeнил]этил } -2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 -b]индoл  436. 8-fluorop-1, 2,3-trimethyl-5 - {2- [4- (triflumethyl) phenyl] ethyl} -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 -b ] indole
437. 6-фтop-l,2,3-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  437. 6-fluorop-l, 2,3-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-W-pyrido [4,3-b] indole
438. 2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  438. 2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
439. 2-этил-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  439. 2-ethyl-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
440. 2,3,7,9-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  440. 2,3,7,9-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
441. 2-этил-3,7,9-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  441. 2-ethyl-3,7,9-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
442. 2,3,8-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  442. 2,3,8-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
443. 2-этил-3,8-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  443. 2-ethyl-3,8-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
444. 8-этил-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3-b] индол  444. 8-ethyl-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
445. 2,3,6,9-тeтpaмeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3-b] индол  445. 2,3,6,9-tetramethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
122 122
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
446. 2-этил-3,6,9-тpимeтил-5-{2-[4-(τpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-446. 2-ethyl-3,6,9-trimethyl-5- {2- [4- (τ-trifomethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-
1 Н-пири до [4,3 -b] индол 1 H-Piri to [4.3-b] indole
447. 2,3,6-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  447. 2,3,6-trimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-bjindole
448. 2-этил-3,6-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  448. 2-ethyl-3,6-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
449. 8-мeтoкcи-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -b]индoл  449. 8-methoxy-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3-b] indole
450. 8-фтop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  450. 8-fluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Ш-pyrido [4,3-bjindole
451. 2-этил-8-фтop-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -b]индoл  451. 2-ethyl-8-fluoro-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3 -b ] indole
452. 8-xлop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  452. 8-chlorop-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
453. 6-фтop-2,3 -димeтил-5- { 2-[4-(тpифтopмeтил)фeнил]этил } -2,3 ,4,5 -тетрагидро- 1 H- пиридо [4,3 -bjиндол  453. 6-fluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-bjindole
454. 2-этил-6-фтop-3-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -bjиндол  454. 2-ethyl-6-fluoro-3-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3-bjindole
455. 6-xлop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  455. 6-chlorop-2,3-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
456. 6,8-дифтop-2,3-димeтил-5-{2-[4-(тpифтopмeтил)фeнилJэтил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  456. 6,8-difluoro-2,3-dimethyl-5- {2- [4- (triflumethyl) phenylJetyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
457. 6-фтop-2,3,9-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  457. 6-fluoro-2,3,9-trimethyl-5- {2- [4- (tri-methyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
458. 1 ,2-димeтил-5- { 2- [4-(тpифтopмeтил)фeнил] этил } -2,3 ,4,5-тeтpaгидpo- 1 H- пиридо [4,3 -bjиндол  458. 1, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-bjindole
459. l,2,8-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнилJэтил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4, 3 -b] индол  459. l, 2,8-trimethyl-5- {2- [4- (triflumethyl) phenylJetyl} -2,3,4,5-tetrahydro-Sh-pyrido [4, 3-b] indole
460. 8-этил-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнилJэтил}-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] индол  460. 8-ethyl-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenylJetyl} -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
461. l,2,6-тpимeтил-5-{2-[4-(тpифтopмeтил)фeнилJэтил}-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  461. l, 2,6-trimethyl-5- {2- [4- (triflumethyl) phenylJetyl} -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
462. 8-мeтoкcи-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- 1 Н-пиридо [4,3 -bjиндол  462. 8-methoxy-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-1 H-pyrido [4,3-bjindole
123 123
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
463. 8-фтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл 463. 8-fluor-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
464. 8-xлop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  464. 8-chlorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
465. 6-фтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  465. 6-fluorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
466. 6-xлop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3.,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  466. 6-chlorop-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2.3., 4,5-tetrahydro-Sh-pyrido [4,3-b] indole
467. 6,8-дифтop-l,2-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-2,3,4,5-тeтpaгидpo- Ш-пиpидo[4,3-b]индoл  467. 6,8-difluoro-l, 2-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -2,3,4,5-tetrahydro-S-pyrido [4,3-b] indole
468. 12-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  468. 12-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
469. 2,12-димeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-6,7,8,9,10,l l-гeкcaгидpo-5H- 7,1 l-эпиминoциклooктa[b]индoл  469. 2,12-dimethyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -6,7,8,9,10, l l-hexahydro-5H-7.1 l-epiminocyclooct [b] indole
470. l l-мeтил-5-{2-[4-(тpифтopмeтил)фeнил]этил}-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  470. l l-methyl-5- {2- [4- (triflumethyl) phenyl] ethyl} -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
471. l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 471. l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
472. l,2,3,8-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл472. l, 2,3,8-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
473. l,2,3,6-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл473. l, 2,3,6-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
474. 8-мeтoкcи-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 474. 8-methoxy-l, 2,3-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
475. 8-фтop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  475. 8-fluor-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
476. 8-xлop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  476. 8-chlorop-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
477. 6-фтop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  477. 6-fluoro-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
478. 6-xлop-l,2,3-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  478. 6-chlorop-l, 2,3-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
479. 2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 479. 2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
480. 2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл480. 2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
481. 2-бeнзил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл481. 2-benzyl-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
482. 2,3,7,9-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл482. 2,3,7,9-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
483. 2-этил-3,7,9-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 483. 2-ethyl-3,7,9-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
124 124
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
484. 2,3,8-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл484. 2,3,8-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
485. 2-этил-3,8-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол 485. 2-ethyl-3,8-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
486. 8-этил-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  486. 8-ethyl-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
487. 2,8-диэтил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  487. 2,8-diethyl-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
488. 2,3,6,9-тeтpaмeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 488. 2,3,6,9-tetramethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
489. 2-этил-3,6,9-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 489. 2-ethyl-3,6,9-trimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
490. 2,3,6-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 490. 2,3,6-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
491. 2-этил-3,6-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 491. 2-ethyl-3,6-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
492. 8-мeтoкcи-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  492. 8-methoxy-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
493. 2-этил-8-мeтoкcи-3 -мeтил-5 -(3 -фeнилпpoпил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  493. 2-ethyl-8-methoxy-3-methyl-5 - (3-phenylpropyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
494. 8-фтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  494. 8-fluoro-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
495. 2-этил-8-фтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  495. 2-ethyl-8-fluoro-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
496. 8-xлop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  496. 8-chlorop-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
497. 8-xлop-2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  497. 8-chlorop-2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
498. 6-фтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  498. 6-fluoro-2,3-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
499. 2-этил-6-фтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  499. 2-ethyl-6-fluoro-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
500. 6-xлop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  500. 6-chlorop-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
501. 6-xлop-2-этил-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  501. 6-chlorop-2-ethyl-3-methyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
502. 6,8-дифтop-2,3-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  502. 6,8-difluoro-2,3-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
125 125
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
503. 2-этил-6,8-дифтop-3-мeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 503. 2-ethyl-6,8-difop-3-methyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
504. 6-фтop-2,3,9-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидp.o-Ш-пиpидo[4,3- b] индол  504. 6-fluoro-2,3,9-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro.o-III-pyrido [4,3-b] indole
505. 2-этил-6-фтop-3,9-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  505. 2-ethyl-6-fluoro-3,9-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
506. l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 506. l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
507. l,2,8-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл507. l, 2,8-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
508. 8-этил-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 508. 8-ethyl-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
509. l,2,6-тpимeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 509. l, 2,6-trimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
510. 8-мeтoкcи-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 510. 8-methoxy-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
511. 8-фтop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  511. 8-fluor-l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
512. 8-xлop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  512. 8-chlorop-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
513. 6-фтop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  513. 6-fluorop-l, 2-dimethyl-5- (3-phenyl-propyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
514. 6-xлop-l,2-димeтил-5-(3-фeнилпpoпил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  514. 6-chlorop-l, 2-dimethyl-5- (3-phenylpropyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
515. 6,8-дифтop- 1 ,2-димeтил-5 -(3 -фeнилпpoпил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол  515. 6,8-difop-1, 2-dimethyl-5 - (3-phenyl-propyl) -2.3, 4,5-tetrahydro-1 H-pyrido [4,3-b] indole
516. l,2-димeтил-8-(мeтилcyльфoнил)-5-(3-фeнилпpoпил)-2,3,4,5.-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  516. l, 2-dimethyl-8- (methylcylphonyl) -5- (3-phenylpropyl) -2,3,4,5.-tetrahydro-Sh-pyrido [4,3 -b] indole
517. 12-мeтил-5-(3-фeнилпpoпил)-6,7, 8,9,10,1 l-reкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  517. 12-methyl-5- (3-phenyl-propyl) -6,7, 8,9,10,1 l-rehydro-5H-7, l 1-epiminocyclooct [b] indole
518. 2,12-димeтил-5-(3-фeнилпpoпил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  518. 2,12-dimethyl-5- (3-phenyl-propyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
519. 1 l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  519. 1 l-methyl-5- (3-phenyl-propyl) -5,6,7,8,9,9-recahydro-7,10-epiminocyclohepta [b] indole
520. 2,11 -димeтил-5-(3-фeнилпpoпил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  520. 2,11-dimethyl-5- (3-phenyl-propyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
521. 2-мeтoкcи-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  521. 2-methoxy-l l-methyl-5- (3-phenyl-propyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
126 126
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
522. 2-фтop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b] индол 522. 2-ftop-l l-methyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-rehydro-7,10-epiminocyclogepth [b] indole
523. 2-xлop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  523. 2-chlorop-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
524. l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  524. l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
525. l,2,3,8-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  525. l, 2,3,8-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
526. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  526. l, 2,3,6-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
527. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  527. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
528. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  528. 8-fluor-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
529. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  529. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
530. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  530. 6-fluorop-l, 2,3-trimethyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
531. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  531. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
532. 2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 532. 2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
533. 2-этил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 533. 2-ethyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
534. 2-бeнзил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  534. 2-benzyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
535. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  535. 2,3,7,9-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
536. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  536. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
537. 2,3,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  537. 2,3,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
538. 2-этил-3 , 8 - диметил- 5 -(2-пиpи дин-2-ил этил)-2 ,3,4,5 -тетраги дро- 1 Н-пири до [4,3 - b] индол  538. 2-ethyl-3, 8-dimethyl-5 - (2-pyr din-2-yl ethyl) -2, 3,4,5-tetrages dro-1 N-pyri to [4,3 - b] indole
539. 8-этил-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  539. 8-ethyl-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
127 127
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
540. 2,8-диэтил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 540. 2,8-diethyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
541. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  541. 2,3,6,9-tetramethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
542. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  542. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
543. 2,3,6-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  543. 2,3,6-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
544. 2-этил-3,6-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  544. 2-ethyl-3,6-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
545. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  545. 8-methoxy-2,3-dimethyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
546. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл  546. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
547. 8-фтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  547. 8-fluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
548. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  548. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
549. 8-xлop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  549. 8-chlorop-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
550. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpa"гидpo-lH-пиpидo[4,3- b] индол  550. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-2-ylethyl) -2,3,4,5-tetra "hydropo-lH-pyrido [4,3-b] indole
551. 8-бpoм-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  551. 8-bromo-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
552. 6-фтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  552. 6-fluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
553. 2-этил-6-фтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3 -b] индол  553. 2-ethyl-6-fluoro-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
554. 6-xлop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  554. 6-chlorop-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
555. 6-xлop-2-этил-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  555. 6-chlorop-2-ethyl-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
556. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  556. 6,8-difluoro-2,3-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
128 128
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
557. 2-этил-6,8-дифтop-3-мeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол 557. 2-ethyl-6,8-difop-3-methyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
558. 6-фтop-2,3 ,9-тpимeтил-5-(2-пиpидин-2-илэтил)*-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - bjиндол 558. 6-fluoro-2,3, 9-trimethyl-5- (2-pyridin-2-yl-ethyl) * -2,3, 4,5-tetrahydro-1 N-pyrido [4,3 - bjindol
559. 2-этил-6-фтop-3,9-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  559. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
560. l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 560. l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
561. l,2,8-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 561. l, 2,8-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
562. 8-этил-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  562. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
563. l,2,6-тpимeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  563. l, 2,6-trimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
564. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  564. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
565. 8-этoкcи-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  565. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
566. 8-фтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  566. 8-fluor-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
567. 8-xлop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  567. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
568. 8-бpoм-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  568. 8-bromo-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
569. 6-фтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  569. 6-fluoro-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
570. 6-xлop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  570. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
571. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3 -b] индол  571. 6,8-difluoro-l, 2-dimethyl-5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
572. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-2-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  572. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-2-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
573. 12-мeтил-5-(2-пиpидин-2-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7Д 1- эпиминoциклooктa[b] индол  573. 12-methyl-5- (2-pyridin-2-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7D 1-epiminocyclooct [b] indole
574. 2,12-димeтил-5-(2-пиpидин-2-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7Д 1- эпиминoциклooктa[b]индoл  574. 2,12-dimethyl-5- (2-pyridin-2-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7D 1-epiminocyclooct [b] indole
129 129
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
575. l l-мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9,10-reкcarидpo-7,10- эпиминoциклoгeптa[b]индoл 575. l l-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9,10-recarcaridpo-7,10-epiminocyclohepta [b] indole
576. 2,1 l-димeтил-5-(2-пиpидин-2-илэтил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  576. 2.1 l-dimethyl-5- (2-pyridin-2-yl-ethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
577. 2-мeтoкcи- 11 -мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  577. 2-methoxy-11-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
578. 2-фтop-l l-мeтил-5-(2-пиpидин-2-илэтил)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  578. 2-fluorop-l-methyl-5- (2-pyridin-2-yl-ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
579. 2-xлop- 11 -мeтил-5-(2-пиpидин-2-илэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  579. 2-chloro-11-methyl-5- (2-pyridin-2-yl-ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
580. l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  580. l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
581. 1,2,3, 8-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  581. 1,2,3, 8-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
582. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  582. l, 2,3,6-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
583. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3 -b] индол  583. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
584. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  584. 8-fluor-l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
585. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  585. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
586. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  586. 6-fluoro-l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
587. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  587. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
588. 2,3 -димeтил-5 -(2-пиpидин-З -илэтил)-2,3 ,4,5-тeтpaгидpo- 1 H-пиpидo[4,3 -bjиндол 588. 2,3-dimethyl-5 - (2-pyridine-3-ethylethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3-bjindole
589. 2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 589. 2-ethyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
590. 2-бeнзил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  590. 2-benzyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
591. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  591. 2,3,7,9-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
592. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  592. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
130 130
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
593. 2,3,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 593. 2,3,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
594. 2-этил-3,8-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  594. 2-ethyl-3,8-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
595. 8-этил-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  595. 8-ethyl-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
596. 2,8-диэтил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  596. 2,8-diethyl-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
597. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  597. 2,3,6,9-tetramethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
598. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  598. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
599. 2,3,6-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  599. 2,3,6-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
600. 2-этил-3,6-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл  600. 2-ethyl-3,6-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
601. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  601. 8-methoxy-2,3-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
602. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  602. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
603. 8-фтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  603. 8-fluoro-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
604. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  604. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
605. 8-xлop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  605. 8-chlorop-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
606. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  606. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
607. 8-бpoм-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  607. 8-bromo-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
608. 6-фтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  608. 6-fluoro-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
609. 2-этил-6-фтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  609. 2-ethyl-6-fluoro-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
131 131
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
610. 6-xлop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 610. 6-chlorop-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
611. 6-xлop-2-этил-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  611. 6-chlorop-2-ethyl-3-methyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
612. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  612. 6,8-difluoro-2,3-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
613. 2-этил-6,8-дифтop-3-мeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо [4, 3 -b] индол  613. 2-ethyl-6,8-difop-3-methyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
614. 6-фтop-2,3,9-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  614. 6-fluoro-2,3,9-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
615. 2-этил-6-фтop-3,9-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  615. 2-ethyl-6-fluoro-3,9-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
616. l,2-димeтил-5-(2-пиpидин-3-илэтил)=2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 616. l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) = 2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
617. 1,2,8-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-1H-пиpидo[4,3- b]индол 617. 1,2,8-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole
618. 8-этил-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  618. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
619. l,2,6-тpимeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  619. l, 2,6-trimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
620. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  620. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
621. 8-этoкcи-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  621. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
622. 8-фтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  622. 8-fluoro-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
623. 8-xлop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  623. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
624. 8-бpoм-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  624. 8-bromo-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
625. 6-фтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  625. 6-fluorop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
626. 6-xлop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  626. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
627. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  627. 6,8-diptop-l, 2-dimethyl-5- (2-pyridin-3-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
132 132
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
628. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-3-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол 628. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-3-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
629. 12-мeтил-5-(2-пиpидин-3-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  629. 12-methyl-5- (2-pyridin-3-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
630. 2,12-димeтил-5-(2-пиpидин-3-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  630. 2,12-dimethyl-5- (2-pyridin-3-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
631. 1 l-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-reкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  631. 1 l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-recahydro-7,10-epiminocyclohepta [b] indole
632. 2Д l-димeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгид£ю-7,10- эпиминoциклoгeптa[b] индол  632. 2D l-dimethyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexagide £ 10-7,10-epiminocyclohepta [b] indole
633. 2-мeтoкcи- 11 -мeтил-5 -(2-пиpидин-З -илэтил)-5 ,6,7, 8 ,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  633. 2-methoxy-11-methyl-5 - (2-pyridine-3-ethylethyl) -5, 6,7, 8, 9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
634. 2-фтop-l l-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  634. 2-fluorop-l l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
635. 2-xлop-l l-мeтил-5-(2-пиpидин-3-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  635. 2-chlorop-l l-methyl-5- (2-pyridin-3-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
636. l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  636. l, 2,3-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
637. l,2,3,8-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  637. l, 2,3,8-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
638. l,2,3,6-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  638. l, 2,3,6-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
639. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  639. 8-methoxy-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
640. 8-фтop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол  640.8-fluorop-l, 2,3-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetraparidro-lH-pyrido [4,3-b] indole
641. 8-xлop-l,2,3-тpимeтил-5-(2-пиpидин«4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  641. 8-chlorop-l, 2,3-trimethyl-5- (2-pyridine "4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
642. 6-фтop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил).-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  642. 6-fluoro-l, 2,3-trimethyl-5- (2-pyridin-4-yl-ethyl) .- 2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
643. 6-xлop-l,2,3-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  643. 6-chlorop-l, 2,3-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
644. 2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 644. 2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
645. 2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 645. 2-ethyl-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
133 133
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
646. 2-бeнзил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол 646. 2-benzyl-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
647. 2,3,7,9-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  647. 2,3,7,9-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
648. 2-этил-3,7,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  648. 2-ethyl-3,7,9-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
649. 2,3,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  649. 2,3,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
650. 2-этил-3,8-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  650. 2-ethyl-3,8-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
651. 8-этил-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  651. 8-ethyl-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
652. 2,8-диэтил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  652. 2,8-diethyl-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
653. 2,3,6,9-тeтpaмeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  653. 2,3,6,9-tetramethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
654. 2-этил-3,6,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  654. 2-ethyl-3,6,9-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
655. .2,3,6-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  655. .2,3,6-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
656. 2-этил-3,6-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  656. 2-ethyl-3,6-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
657. 8-мeтoкcи-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  657. 8-methoxy-2,3-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
658. 2-этил-8-мeтoкcи-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  658. 2-ethyl-8-methoxy-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
659. 8-этoкcи-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  659. 8-ethoxy-2,3-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
660. 8-фтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  660. 8-fluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
661. 2-этил-8-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  661. 2-ethyl-8-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
662. 8-xлop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  662. 8-chlorop-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
134 134
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
663. 8-xлop-2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 663. 8-chlorop-2-ethyl-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
664. 8-бpoм-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  664. 8-bromo-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
665. 6-фтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  665. 6-fluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
666. 2-этил-6-фтop-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  666. 2-ethyl-6-fluoro-3-methyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
667. 6-xлop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  667. 6-chlorop-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
668. 6-xлop-2-этил-3-мeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  668. 6-chlorop-2-ethyl-3-methyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
669. 6,8-дифтop-2,3-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтparидpo-lH- пиpидo[4,3-b]индoл  669. 6,8-difluoro-2,3-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetraparidro-lH-pyrido [4,3-b] indole
670. 6-фтop-2,3,9-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  670. 6-fluoro-2,3,9-trimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
671. l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 671. l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
672. l,2,8-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 672. l, 2,8-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
673. 8-этил-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  673. 8-ethyl-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
674. l,2,6-тpимeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  674. l, 2,6-trimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
675. 8-мeтoкcи-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пири до [4 , 3 -b] индол  675. 8-methoxy-l, 2-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-Sh-pyri to [4, 3-b] indole
676. 8-этoкcи-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  676. 8-ethoxy-l, 2-dimethyl-5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
677. 8-фтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-* b] индол 677. 8-fluor-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3- * b] indole
678. 8-xлop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  678. 8-chlorop-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
679. 8-бpoм-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  679. 8-bromo-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
680. 6-фтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  680. 6-fluoro-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
135 135
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
681. 6-xлop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 681. 6-chlorop-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
682. 6,8-дифтop-l,2-димeтил-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  682. 6,8-difluoro-l, 2-dimethyl-5- (2-pyridin-4-yl-ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
683. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-пиpидин-4-илэтил)-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -bjиндол  683. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-pyridin-4-ylethyl) -2,3,4,5-tetrahydro-Ш-pyrido [4,3-bjindole
684. 12-мeтил-5-(2-пиpидин-4-илэтил)-6,7,8,9, 10,11 -reкcaгидpo-5H-7, 11 - эпиминoциклooктa[b]индoл  684. 12-methyl-5- (2-pyridin-4-yl-ethyl) -6,7,8,9, 10,11-rehydro-5H-7, 11 - epiminocyclooct [b] indole
685. 2,12-димeтил-5-(2-пиpидин-4-илэтил)-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  685. 2,12-dimethyl-5- (2-pyridin-4-yl-ethyl) -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
686. l l-мeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b]индoл  686. l l-methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
687. 2,11 -димeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  687. 2,11-dimethyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
688. 2-мeтoкcи-l l-мeтил-5-(2-пиpидин-4-илэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  688. 2-methoxy-l l-methyl-5- (2-pyridin-4-yl-ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [b] indole
689. 2-фтop-l l-мeтил-5-(2-пиpидин-4-илэтил)-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  689. 2-ftop-l l-methyl-5- (2-pyridin-4-yl-ethyl) -5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
690. 2-xлop-l l-мeтил-5-(2-пиpидин-4-илэтил)-5, 6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  690. 2-chlorop-l l-methyl-5- (2-pyridin-4-yl-ethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
691. 2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  691. 2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
692. 2,3,7,9-тeтpaмeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  692. 2,3,7,9-tetramethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
693. 2,3,8-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  693. 2,3,8-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
694. 2,3,6,9-тeтpaмeтил-5-[2-(6-мeтилпиpйдин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  694. 2,3,6,9-tetramethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
695. 2,3,6-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b]индoл  695. 2,3,6-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3 -b] indole
696. 8-мeтoкcи-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  696. 8-methoxy-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
697. 8-фтop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  697. 8-fluoro-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
136 136
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
698. 8-xлop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4 , 3 -b] индол 698. 8-chlorop-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4, 3-b] indole
699. 6-фтop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  699. 6-fluoro-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
700. 6-xлop-2,3-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  700. 6-chlorop-2,3-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
701. 6-фтop-2,3,9-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  701. 6-fluoro-2,3,9-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b ] indole
702. l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  702. l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
703. l,2,8-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индол  703. l, 2,8-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
704. 8-этил-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  704. 8-ethyl-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
705. l,2,6-тpимeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  705. l, 2,6-trimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
706. 8-мeтoкcи-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  706. 8-methoxy-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
707. 8-фтop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиpидo[4,3-b]индoл  707. 8-fluoro-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
708. 8-xлop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пири до [4,3-b]индoл  708. 8-chlorop-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyri before [4,3-b] indole
709. 6-фтop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  709. 6-fluoro-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
710. 6-xлop-l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  710. 6-chlorop-l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
711. 6,8-дифтop- 1 ,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-2,3,4,5-тeтpaгидpo- 1 H- пиридо [4,3 -b]индoл  711. 6,8-diptor-1, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -2,3,4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
712. l,2-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-8-(мeтилcyльфoнил)-2,3,4,5- тетрагидро- 1 Н-пиридо [4,3 -b] индол  712. l, 2-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -8- (methylcylphonyl) -2,3,4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
713. 2,12-димeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  713. 2,12-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b ] indole
714. 11 -мeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  714. 11-methyl-5- [2- (6-methylpyridin-3-yl) ethyl] -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
137 137
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
715. 2,11 -димeтил-5-[2-(6-мeτилпиpидин-3-ил)этил]-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол 715. 2,11-dimethyl-5- [2- (6-methylpyridin-3-yl) ethyl] -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
716. 2-фтop-l l-мeтил-5-[2-(6-мeтилпиpидин-3-ил)этил]-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[b] индол  716. 2-fluorop-l-methyl-5- [2- (6-methylpyridin-3-yl) ethyl] -5,6,7,8,9,10-hexahydro-7,10-epiminocyclogen [b] indole
717. l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 717. l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
718. l,2,3,8-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл718. l, 2,3,8-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
719. l,2,3,6-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл719. l, 2,3,6-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
720. 8-мeтoкcи-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 720. 8-methoxy-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
721. 8-фтop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  721. 8-fluoro-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
722. 8-xлop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  722. 8-chlorop-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
723. 6-фтop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  723. 6-fluoro-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
724. 6-xлop-l,2,3-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  724. 6-chlorop-l, 2,3-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
725. 2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 725. 2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
726. 2,3,7,9-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл726. 2,3,7,9-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
727. 2,3,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл727. 2,3,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
728. 8-этил-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл728. 8-ethyl-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
729. 2,3,6,9-тeтpaмeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл729. 2,3,6,9-tetramethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
730. 2,3,6-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл730. 2,3,6-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
731. 8-мeтoкcи-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 731. 8-methoxy-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
732. 8-фтop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 732. 8-fluoro-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
733. 8-xлop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл733. 8-chlorop-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
734. 6-фтop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл734. 6-fluoro-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
735. 6-xлop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл735. 6-chlorop-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
736. 6,8-дифтop-2,3-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 736. 6,8-difluoro-2,3-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
737. 6-фтop-2,3,9-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  737. 6-fluoro-2,3,9-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
738. 1 ,2-димeтил-5 -(2-фeнoкcиэтил)-2,3 ,455 -тетрагидро- 1 Н-пиридо [4,3 -b] индол738. 1, 2-dimethyl-5 - (2-phenoxyethyl) -2.3, 4 5 5-tetrahydro-1 H-pyrido [4.3-b] indole
739. l,2,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 739. l, 2,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
138 138
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
740. 8-этил-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл740. 8-ethyl-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
741. 1 ,2,6-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл741. 1, 2,6-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
742. 8-мeтoкcи-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтparидpo-lH-пиpидo[4,3- b] индол 742. 8-methoxy-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetra-para-lH-pyrido [4,3-b] indole
743. 8-фтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 743. 8-fluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
744. 8-xлop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл744. 8-chlorop-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
745. 6-фтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл745. 6-fluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
746. 6-xлop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл746. 6-chlorop-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
747. 6,8-дифтop-l,2-димeтил-5-(2-фeнoкcиэтил)-2,3~4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 747. 6,8-difluoro-l, 2-dimethyl-5- (2-phenoxyethyl) -2,3 ~ 4,5-tetrahydro-lH-pyrido [4,3-b] indole
748. l,2-димeтил-8-(мeтилcyльфoнил)-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3 -b] индол  748. l, 2-dimethyl-8- (methylcylphonyl) -5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3 -b] indole
749. 12-мeтил-5-(2-фeнoкcиэтил)-6, 7,8,9,10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  749. 12-methyl-5- (2-phenoxyethyl) -6, 7,8,9,10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
750. 2,12-димeтил-5-(2-фeнoкcиэтил)-6,7,8,9,10,l 1 -гeкcaгидpo-5H-7 ,11- эпиминoциклooктa[b] индол  750. 2,12-dimethyl-5- (2-phenoxyethyl) -6,7,8,9,10, l 1 -hexahydro-5H-7, 11-epiminocyclooct [b] indole
751. 11 -мeтил-5-(2-фeнoкcиэтил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  751. 11-methyl-5- (2-phenoxyethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
752. 2,11 -димeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9, 10-гejccaгидpo-7, 10- эпиминoциклoгeптa[b] индол  752. 2,11-dimethyl-5- (2-phenoxyethyl) -5,6,7,8,9, 10-hejccahydro-7, 10-epiminocyclohepta [b] indole
753. 2-мeтoкcи- 11 -мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  753. 2-methoxy-11-methyl-5- (2-phenoxyethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
754. 2-фтop- 11 -мeтил-5-(2-фeнoкcиэтил)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  754. 2-fluoro-11-methyl-5- (2-phenoxyethyl) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
755. 2-xлop-l 1 -мeтил-5-(2-фeнoкcиэтил)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  755. 2-chlorop-l 1-methyl-5- (2-phenoxyethyl) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [b] indole
756. 5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  756. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
757. 5-[2-(3-фтopфeнил)этил]-l,2,3,8-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  757. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3,8-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
758. 5-[2-(3-фтopфeнил)этил]-l,2,3,6-тeтpaмeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  758. 5- [2- (3-fluorophenyl) ethyl] -l, 2,3,6-tetramethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
759. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -b] индол  759. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3 -b] indole
139 139
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
760. 8-фтop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-b]индoл 760. 8-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
761. 8-xлop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индол  761. 8-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
762. 6-фтop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  762. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
763. 6-xлop-5-[2-(3-фтopфeнил)этил]-l,2,3-тpимeтил-2,3,4,5-тeтpaгидpo-lH- пиридо[4,3-b]индoл  763. 6-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2,3-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
764. 5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 764. 5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
765. 5-[2-(3-фтopфeнил)этил]-2,3,7,9-тeтp*aмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол 765. 5- [2- (3-fluorophenyl) ethyl] -2,3,7,9-tetra * methyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
766. 5-[2-(3-фтopфeнил)этил]-2,3,8-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  766. 5- [2- (3-fluorophenyl) ethyl] -2,3,8-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
767. 8-этил-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  767. 8-ethyl-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
768. 5-[2-(3-фтopфeнил)этил]-2,3,6,9-тeтpaмeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индол  768. 5- [2- (3-fluorophenyl) ethyl] -2,3,6,9-tetramethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
769. 5-[2-(3-фтopфeнил)этил]-2,3,6-тpимeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  769. 5- [2- (3-fluorophenyl) ethyl] -2,3,6-trimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
770. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо[4,3-bjиндол  770. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-bjindole
771. 8-фтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индол  771. 8-fluoro-5- [2- (3-fluoro-phenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
772. 8-xлop-5 - [2-(3-фтopфeнил)этил] -2,3 -димeтил-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - bjиндол  772. 8-chlorop-5 - [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - bjindole
773. 6-фтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  773. 6-fluoro-5- [2- (3-fluoro-phenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
774. 6-xлop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  774. 6-chlorop-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
775. 6,8-дифтop-5-[2-(3-фтopфeнил)этил]-2,3-димeтил-2,3,4,5-тeтpaгидpo-lH- пиридо [4,3 -bjиндол  775. 6,8-difop-5- [2- (3-fluorophenyl) ethyl] -2,3-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-bjindole
776. 6-фтop-5-[2-(3-фтopфeнил)этил]-2,3,9-тpимeтил-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  776. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -2,3,9-trimethyl-2,3,4,5-tetrahydro-Sh-pyrido [4,3-b] indole
777. 5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл  777. 5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
140 140
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
778. 5-[2-(3-фтopфeнил)этил]-l,2,8-тpимeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 778. 5- [2- (3-fluorophenyl) ethyl] -l, 2,8-trimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
779. 8-этил-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  779. 8-ethyl-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
780. 5- [2-(3 -фтopфeнил)этил] - 1 ,2,6-тpимeтил-2,3 ,4 Д-тетрагидро- 1 Н-пиридо [4,3 - b] индол  780. 5- [2- (3-fluorophenyl) ethyl] - 1, 2,6-trimethyl-2,3, 4 D-tetrahydro-1 H-pyrido [4,3 - b] indole
781. 5-[2-(3-фтopфeнил)этил]-8-мeтoкcи-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш- пиридо [4,3 -b] индол  781. 5- [2- (3-fluorophenyl) ethyl] -8-methoxy-l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
782. 8-фтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  782. 8-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
783. 8-xлop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  783. 8-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
784. 6-фтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  784. 6-fluorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
785. 6-xлop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  785. 6-chlorop-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
786. 6,8-дифтop-5-[2-(3-фтopфeнил)этил]-l,2-димeтил-2,3,4,5-тeтparидpo-Ш- пиpидo[4,3 -b] индол  786. 6,8-difluoro-5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-2,3,4,5-tetra-para-Sh-pyrido [4,3-b] indole
787. 5-[2-(3-фтopфeнил)этил]-l,2-димeтил-8-(мeтилcyльфoнил)-2,3,4,5-тeтpaгидpo-Ш- пиpидo[4,3-b]индoл  787. 5- [2- (3-fluorophenyl) ethyl] -l, 2-dimethyl-8- (methylcylphonyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
788. 5-[2-(3-фтopфeнил)этил]-12-мeтил-6,7, 8,9, 10,1 l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b] индол  788. 5- [2- (3-fluorophenyl) ethyl] -12-methyl-6,7, 8,9, 10,1 l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
789. 5-[2-(3-фтopфeнил)этил]-2,12-димeтил-6,7,8,9,10,l l-гeкcaгидpo-5H-7,l 1- эпиминoциклooктa[b]индoл  789. 5- [2- (3-fluorophenyl) ethyl] -2,12-dimethyl-6,7,8,9,10, l l-hexahydro-5H-7, l 1-epiminocyclooct [b] indole
790. 5-[2-(3-фтopфeнил)этил]-l l-мeтил-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминоциклогептаfb] индол  790. 5- [2- (3-fluorophenyl) ethyl] -l l-methyl-5,6,7, 8,9,10-hexahydro-7, 10-epiminocycloheptfb] indole
791. 5-[2-(3-фтopфeнил)этил]-2, 11 -димeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  791. 5- [2- (3-fluorophenyl) ethyl] -2, 11-dimethyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
792. 5-[2-(3-фтopфeнил)этил]-2-мeтoкcи-l l-мeтил-5,6, 7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b]индoл  792. 5- [2- (3-fluorophenyl) ethyl] -2-methoxy-l l-methyl-5,6, 7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
793. 2-фтop-5 - [2-(3 -фтopфeнил)этил]- 11 -мeтил-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  793. 2-fluorop-5 - [2- (3-fluorophenyl) ethyl] - 11-methyl-5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
794. 2-xлop-5-[2-(3-фтopфeнил)этил]- 11 -мeтил-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[b] индол  794. 2-chlorop-5- [2- (3-fluorophenyl) ethyl] - 11-methyl-5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [b] indole
141 141
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
795. 2-циклoгeкcил-3-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 795. 2-cyclohexyl-3-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
796. 2-изoпpoпил-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7, 8,9,10-reкcaгидpo-7, 10- эпиминoциклoгeптa[6] индол  796. 2-isopropyl-l l-methyl-5- (3-phenylpropyl) -5,6,7, 8,9,10-reccahydro-7, 10-epiminocyclohepta [6] indole
797. 2,4-дифтop-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол  797. 2,4-difltop-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
798. l-xлop-4,l l-димeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[6] индол  798. l-chlorop-4, l l-dimethyl-5- (3-phenyl-propyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [6] indole
799. 4-фтop-l,l l-димeтил-5-(3-фeнилпpoпил)-5,6,7,$,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол  799. 4-fluorop-l, l l-dimethyl-5- (3-phenyl-propyl) -5,6,7, $, 9,10-hexahydro-7,10-epiminocyclogen [ό] indole
800. 2,4, 11 -тpимeтил-5-(3-фeнилпpoпил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол  800. 2,4, 11-trimethyl-5- (3-phenyl-propyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
801. 2-этил-l l-мeтил-5-(3-фeнилпpoпил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό]индoл  801. 2-ethyl-l l-methyl-5- (3-phenylpropyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
802. 11 -циклoreкcил-5-(3 -фeнилпpoпил)-5 ,6,7,8 ,9, 10-гeкcaгидpo-7, 10- эпиминoциклoreптa[ό] индол  802. 11 -cyclorexyl-5- (3-phenylpropyl) -5, 6,7,8, 9, 10-hexahydro-7, 10-epiminocyclorepta [ό] indole
803. 1 l-бeнзил-5-(3-фeнилпpoпил)-5,6,7,8-,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό]индoл  803. 1 l-benzyl-5- (3-phenyl-propyl) -5,6,7,8-, 9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
804. 2-мeтoкcи- 11 -мeтил-5-(2-фeнилэтoкcи)-5,6,7,8,9. , 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό]индoл 804. 2-Methoxy-11-methyl-5- (2-phenylethoxy) -5,6,7,8,9 . , 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
805. 2-фтop-l l-мeтил-5-(2-фeнoкcиэтил)-5,6,7,8,9Д0-гeкcaгидpo-6,9- эпиминoциклoгeптa[ό]индoл  805. 2-fluorop-l l-methyl-5- (2-phenoxyethyl) -5,6,7,8,9D0-hexahydro-6,9-epiminocyclogen [ό] indole
806. 2,3,8-тpимeтил-5-(2-фeнoкcиэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-6]индoл 806. 2,3,8-trimethyl-5- (2-phenoxyethyl) -2,3,4,5-tetrahydro-lH-pyrido [4.3-6] indole
807. 2-мeтил- 11 -мeтил-5-(2-фeнилэтoкcи)-5 ,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[&] индол 807. 2-methyl-11-methyl-5- (2-phenylethoxy) -5, 6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [&] indole
808. 11 -мeтил-5-(2-фeнилэтoкcи)-5,6,7, 8,9,10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[&] индол  808. 11-methyl-5- (2-phenylethoxy) -5,6,7, 8,9,10-hexahydro-7, 10-epiminocyclohepta [&] indole
809. 2-изoпpoпил- 11 -мeтил-5-(2-фeнилэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[δ]индoл  809. 2-isopropyl-11-methyl-5- (2-phenylethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocycle [δ] indole
810. 11 -мeтил-2-этил-5-(2-фeнилэтил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό]индoл  810. 11-methyl-2-ethyl-5- (2-phenylethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
811. 1 l-циклoгeкcил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7Д0- эпиминoциклoгeптa[6] индол  811. 1 l-cyclohexyl-5- (2-phenylethyl) -5,6,7,8,9,10-hexahydro-7D0-epiminocyclohepta [6] indole
812. 1 l-бeнзил-5-(2-фeнилэтил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол  812. 1 l-benzyl-5- (2-phenylethyl) -5,6,7,8,9,9-hexahydro-7,10-epiminocyclohepta [ό] indole
142 142
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
813. 2,11 -димeтил-5-(2-(4-мeтилфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoreптa[ό]индoл 813. 2,11-dimethyl-5- (2- (4-methylphenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclorepta [ό] indole
814. 2,11 -димeтил-5-(2-(2-мeтилфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpoь7, 10- эпиминoциклoгeптa[6]индoл 814. 2.11 -dimetil-5- (2- (2-methylphenyl) ethyl) -5,6,7,8,9, 10-hexahydro s 7, 10- epiminotsiklogepta [6] indol
815. 2,11 -димeтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[6] индол  815. 2,11-dimethyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [6] indole
816. 2,11 -димeтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол  816. 2,11-dimethyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
817. 11 -мeтил-5-(2-(4-мeтилфeнил)этил)-5 ,6,7,8,9, 10-гeкcarидpo-7, 10- эпиминoциклoгeптa[&]индoл  817. 11-methyl-5- (2- (4-methylphenyl) ethyl) -5, 6,7,8,9, 10-hexacaridro-7, 10-epiminocycle [&] indole
818. l l-мeтил-5-(2-(2-мeтилфeнил)этил)-5,6,7,8,9,10-гeкcaгидpo-7,10- эпиминoциклoгeптa[ό] индол  818. l l-methyl-5- (2- (2-methylphenyl) ethyl) -5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta [ό] indole
819. 11 -Meтил-5-(2-(4-фтopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ό] индол  819. 11-Methyl-5- (2- (4-fluorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ό] indole
820. 11 -мeтил-5-(2-(4-xлopфeнил)этил)-5,6,7,8,9, 10-гeкcaгидpo-7, 10- эпиминoциклoгeптa[ά] индол  820. 11-methyl-5- (2- (4-chlorophenyl) ethyl) -5,6,7,8,9, 10-hexahydro-7, 10-epiminocyclohepta [ά] indole
821. l-этил-2-мeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл 821. l-ethyl-2-methyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
822. 2-мeтил-3-этил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл822. 2-methyl-3-ethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
823. l-этил-2,8-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл823. l-ethyl-2,8-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
824. 2,8-димeтил-3-этил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл824. 2,8-Dimethyl-3-ethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
825. l,2-димeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл825. l, 2-dimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
826. l,2,8-тpимeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл826. l, 2,8-trimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
827. 2,3-димeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тёtpaгидpo-Ш-пиpидo[4,3-b]индoл827. 2,3-dimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
828. 2,3,8-тpимeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-tiиpидo[4,3-b]индoл828. 2,3,8-trimethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-tiirido [4,3-b] indole
829. 1 ,2,3 -тpимeтил-5 -(2-(2-фтopфeнил)этил)-2,3 ,4,5 -тетрагидро- 1 Н-пиридо [4,3 - b] индол 829. 1, 2,3-trimethyl-5 - (2- (2-fluorophenyl) ethyl) -2,3, 4,5-tetrahydro-1 H-pyrido [4,3 - b] indole
830. l,2,3,8-тeтpaмeтил-5-(2-(2-фтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  830. l, 2,3,8-tetramethyl-5- (2- (2-fluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
831. 1 ,2-димeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  831. 1, 2-dimethyl-5- (2- (2,4-difertophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
832. l,2,8-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол  832. l, 2,8-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
833. 2,3-димeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4j5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 833. 2,3-dimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4 j 5-tetrahydro-lH-pyrido [4,3-b] indole
143 143
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
834. 2,3,8-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b] индол 834. 2,3,8-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
835. l,2,3-тpимeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  835. l, 2,3-trimethyl-5- (2- (2,4-difluorophenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
836. l,2,3,8-тeтpaмeтил-5-(2-(2,4-дифтopфeнил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  836. l, 2,3,8-tetramethyl-5- (2- (2,4-diferephenyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
837. l,2-димeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл 837. l, 2-dimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
838. l,2,8-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл838. l, 2,8-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
839. 2,3-димeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл839. 2,3-dimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
840. 2,3,8-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл840. 2,3,8-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
841. 1 ,2,3-тpимeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл841. 1, 2,3-trimethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
842. l,2,3,8-тeтpaмeтил-5-(2-(2-нaфтил)этил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл842. l, 2,3,8-tetramethyl-5- (2- (2-naphthyl) ethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
843. l,2-димeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл843. l, 2-dimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
844. l,2,8-тpимeтил-5-(2-(l-нaфтил)этил)-2,3;4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл844. l, 2,8-trimethyl-5- (2- (l-naphthyl) ethyl) -2.3; 4,5-tetrahydro-III-pyrido [4,3-b] indole
845. 2,3-димeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл845. 2,3-dimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
846. 2,3,8-тpимeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгjiдpo-lH-пиpидo[4,3-b]индoл846. 2,3,8-trimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydroxy-lH-pyrido [4,3-b] indole
847. l,2,3-тpимeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл847. l, 2,3-trimethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
848. l,2,3,8-тeтpaмeтил-5-(2-(l-нaфтил)этил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл848. l, 2,3,8-tetramethyl-5- (2- (l-naphthyl) ethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
849. (lR)-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл849. (lR) -l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
850. (lS)-l,2-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл850. (lS) -l, 2-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
851. (lR)-l,2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл851. (lR) -l, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
852. (lS)-l,2,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл852. (lS) -l, 2,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
853. (ЗR)-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3-b]индoл853. (3R) -2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
854. (ЗS)-2,3-димeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл854. (3S) -2,3-dimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
855. (ЗR)-2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл855. (3R) -2,3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
856. (ЗS)-2,3,8-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3-b]индoл856. (3S) -2,3,8-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole
857. (lR,ЗR)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индoл 857. (lR, 3R) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
858. (lR,ЗS)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  858. (lR, ZS) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
859. (lS,ЗR)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол  859. (lS, 3R) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
860. (lS,ЗS)-l,2,3-тpимeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b]индoл  860. (lS, ZS) -l, 2,3-trimethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
144 144
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
861. (lR,ЗR)-l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтpaгидpo-Ш-пиpидo[4,3- b] индол 861. (lR, 3R) -l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
862. (lR,ЗS)-l,2,3,8-тeтpaмeтил-5-(2-фeнилэтил)-2,3,4,5-тeтparидpo-Ш-пиpидo[4,3- b] индол  862. (lR, ZS) -l, 2,3,8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-III-pyrido [4,3-b] indole
863. (1S,ЗR)- 1,2,3, 8-тeтpaмeтил-5-(2-фeнилэтил)-2,3 ,4,5-тeтpaгидpo- lH-пиpидo[4,3- b] индол  863. (1S, 3R) -1,2,3, 8-tetramethyl-5- (2-phenylethyl) -2,3, 4,5-tetrahydrol-lH-pyrido [4,3-b] indole
864. (1S,ЗS)- 1,2,3, 8-тeтpaмeтил-5-(2-фeнилэтйл)-2,3,4,5-тeтpaгидpo-lH-пиpидo[4,3- b]индoл.  864. (1S, 3S) -1,2,3, 8-tetramethyl-5- (2-phenylethyl) -2,3,4,5-tetrahydro-lH-pyrido [4,3-b] indole.
5. Физиологически активные вещества общей формулы I по любому из пп. 1-4, проявляющие свойства антагонистов серотониновых рецепторов 5-HT6.  5. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, showing the properties of antagonists of serotonin receptors 5-HT6.
6. Физиологически активные вещества общей формулы I по любому из пп. 1-4, проявляющие свойства антагонистов серотониновых рецепторов 5-HT7.  6. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, showing the properties of antagonists of serotonin receptors 5-HT7.
7. Физиологически активные вещества общей формулы I по любому из пп. 1-4, проявляющие свойства ингибиторов бутирилхолинэстеразы BChE.  7. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, showing the properties of butyrylcholinesterase BChE inhibitors.
8. Физиологически активные вещества общей формулы I по любому из пп. 1-4, проявляющие свойства эффекторов митохондриальных пор MPTP.  8. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, showing the properties of mitochondrial pore effectors MPTP.
9. Физиологически активные вещества общей формулы I по любому из пп. 1-4, одновременно проявляющие свойства антагонистов серотониновых рецепторов по пп. 5,6 и ингибиторов бутирил холинэстеразы BChE по п. 7.  9. Physiologically active substances of the general formula I according to any one of paragraphs. 1-4, simultaneously exhibiting the properties of serotonin receptor antagonists according to paragraphs. 5,6 and BChE butyryl cholinesterase inhibitors according to claim 7.
10. Физиологически активные вещества общей формулы I по любому из пп. 1-4, одновременно проявляющие свойства антагонистов серотониновых рецепторов по пп. 5,6 и эффекторов митохондриальных пор MPTP по п. 8.  10. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, simultaneously exhibiting the properties of serotonin receptor antagonists according to paragraphs. 5,6 and MPTP mitochondrial pore effectors according to claim 8.
11. Физиологически активные вещества общей формулы I по любому из пп. 1-4, одновременно проявляющие свойства антагонистов серотониновых рецепторов 5-HT6 по п. 5, антагонистов серотониновых рецепторов 5-HT7 по п. 6, ингибиторов бутирилхолинэстеразы BChE по п. 7 и блокаторов митохондриальных пор MPTP по п. 8.  11. Physiologically active substances of General formula I according to any one of paragraphs. 1-4, simultaneously exhibiting the properties of 5-HT6 serotonin receptor antagonists according to claim 5, 5-HT7 serotonin receptor antagonists according to claim 6, BChE butyrylcholinesterase inhibitors according to claim 7 and MPTP mitochondrial pore blockers according to claim 8.
12. Лекарственная субстанция, обладающая физиологической активностью по пп. 5-11 общей формулы I - 1.5.2 по любому из пунктов 1-4, для производства фармацевтических композиций и лекарственных препаратов.  12. A drug substance having physiological activity according to claims. 5-11 of the general formula I - 1.5.2 according to any one of paragraphs 1-4, for the manufacture of pharmaceutical compositions and drugs.
13. Фармацевтическая композиция, содержащая- лекарственную субстанцию по п. 12, и обладающая свойством эффективно воздействовать на серотон-иновые рецепторы по пп. 5, 6, и/или на бутирилхолинэстеразу BuChE по п. 7, и/или на митохондрии по п. 8, и тем самым проявляющая нейропротекторную и когнитивно-стимулирующую активности.  13. A pharmaceutical composition comprising a drug substance according to claim 12, and having the property to effectively act on serotonin receptors according to claims. 5, 6, and / or BuChE butyrylcholinesterase according to claim 7, and / or mitochondria according to claim 8, and thereby exhibiting neuroprotective and cognitively stimulating activity.
145 145
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
14. Способ получения фармацевтической композиции по п. 13, заключающийся в в смешении лекарственной субстанции по п. 12 с инертными наполнителями, стабилизаторами и прочими компонентами композиции. 14. The method of obtaining the pharmaceutical composition according to p. 13, which consists in mixing the medicinal substance according to p. 12 with inert excipients, stabilizers and other components of the composition.
15. Лекарственное средство в виде таблеток, желатиновых капсул, пилюль, порошков, гранул, пероральных растворов или суспензий, сублингвальных и трансбуккальных форм, аэрозолей, имплантатов, местных, трансдермальных, подкожных, внутримышечных, внутривенных, интраназальных, внутриглазных или ректальные форм, помещенных в фармацевтически приемлемую упаковку для лечения и предупреждения нейродегенеративных заболеваний, включающее в свой состав лекарственную субстанцию по п. 12 или фармацевтическую композицию по п. 13.  15. A medicine in the form of tablets, gelatine capsules, pills, powders, granules, oral solutions or suspensions, sublingual and buccal forms, aerosols, implants, local, transdermal, subcutaneous, intramuscular, intravenous, intranasal, intraocular or rectal forms a pharmaceutically acceptable package for the treatment and prevention of neurodegenerative diseases, comprising a drug substance according to claim 12 or a pharmaceutical composition according to claim 13.
16. Способ лечения и предупреждения нейродегенеративных заболеваний у человека или теплокровного животного, патогенез которых связан с дисфункцией серотонинэргической и/или холинэргической системна также с нарушением функций митохондрий, путем введения человеку или теплокровному животному лекарственного средства по п. 15.  16. A method for the treatment and prevention of neurodegenerative diseases in humans or warm-blooded animals, the pathogenesis of which is associated with dysfunction of the serotonergic and / or cholinergic systemic is also associated with dysfunction of the mitochondria, by administering to the person or warm-blooded animal the medicine according to claim 15.
17. Способ лечения и предупреждения нейродегенеративных заболеваний у человека или теплокровного животного по п. 16, вкючающих болезни Альцгеймера и Паркинсона; болезнь (хорею) Хантингтона; рассеянный склероз; мозжечковую дегенерацию; амиотрофический латеральный склероз; деменцию с тельцами Леви; спинальную мускульную атрофию; периферическую нейропатию; губчатый энцефалит («кopoвьe бeшeнcтвo»); СПИД-ассоцииррванную деменцию; мультиинфарктную деменцию; лобно-височную деменцию; лейкоэнцефалопатию; хронические нейродегенеративные заболевания; инсульт; ишемическое, реперфузионное и гипоксическое повреждения мозга; эпилепсию; церебральную ишемию; глаукому; черепно-мозговую травму; синдром Дауна; энцефаломиелит; менингит; энцефалит; нейробластому; шизофрению; депрессию, а также нейрональные повреждения, ассоциированные с аутоиммунными, инфекционными, онкологическими и эндокринными заболеваниями; и прочие нейродегенеративные процессы.  17. A method for the treatment and prevention of neurodegenerative diseases in humans or warm-blooded animals according to claim 16, including Alzheimer's and Parkinson's diseases; Huntington's disease (chorea); multiple sclerosis; cerebellar degeneration; amyotrophic lateral sclerosis; dementia with Levy bodies; spinal muscular atrophy; peripheral neuropathy; spongiform encephalitis (“bovine rabies”); AIDS-associated dementia; multi-infarct dementia; frontotemporal dementia; leukoencephalopathy; chronic neurodegenerative diseases; stroke; ischemic, reperfusion, and hypoxic brain damage; epilepsy cerebral ischemia; glaucoma; traumatic brain injury; Down syndrome; encephalomyelitis; meningitis; encephalitis; neuroblastoma; schizophrenia; depression, as well as neuronal damage associated with autoimmune, infectious, oncological and endocrine diseases; and other neurodegenerative processes.
18. Способ лечения и предупреждения нейродегенеративных процессов у человека или теплокровного животного по п. 16, связанных со старением организма.  18. The method of treatment and prevention of neurodegenerative processes in humans or warm-blooded animals according to claim 16, associated with the aging of the body.
19. Способ лечения и предупреждения нейродегенеративных заболеваний по пунктам 16, 17 и 18 путем введения человеку или теплокровному животному лекарственного средства по п. 12 в дозе 0,005 - 10.0 мг/кг массы тела по крайней мере один раз в день в течение периода, необходимого для достижения терапевтического эффекта.  19. The method of treatment and prevention of neurodegenerative diseases according to paragraphs 16, 17 and 18 by administering to a human or warm-blooded animal the medicine according to claim 12 at a dose of 0.005 to 10.0 mg / kg body weight at least once a day for a period necessary for achieve a therapeutic effect.
146 146
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26) SUBSTITUTE SHEET (RULE 26)
20. Соединения общей формулы I по п. 1, обладающие свойством эффективно воздействовать на серотониновые рецепторы 5-HT6 и/или 5-HT7, и/или на бутирилхолинэстеразу BuChE и/или митохондрии, предназначенные для экспериментального исследования биохимических сигнальных систем и физиологических процессов iп vitrо и iп vivо в качестве ((фармакологических инструментов)). 20. The compounds of general formula I according to claim 1, having the property of effectively acting on 5-HT6 and / or 5-HT7 serotonin receptors and / or on BuChE butyrylcholinesterase and / or mitochondria, intended for experimental study of biochemical signal systems and physiological processes vitro and ip vivo as ((pharmacological tools)).
21. Способ получения соединений формулы 1.1 в соответствие со следующей схемой:  21. The method of obtaining compounds of formula 1.1 in accordance with the following scheme:
Figure imgf000149_0001
Figure imgf000149_0001
X = -CH2CH2-Hal, -CH=CH2, еtс.  X = -CH2CH2-Hal, -CH = CH2, etc.
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
22. Способ получения соединений формулы 1.2 в соответствие со следующей схемой:  22. The method of obtaining compounds of formula 1.2 in accordance with the following scheme:
Figure imgf000149_0002
Figure imgf000149_0002
Figure imgf000149_0003
Figure imgf000149_0003
X = CH2CH2-Hal, CH=CH2, еtс. X = CH2CH2-Hal, CH = CH2, etc.
Figure imgf000149_0004
Figure imgf000149_0004
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
23. Способ получения соединений формулы J.З в соответствие со следующей схемой:  23. The method of obtaining compounds of formula J. 3 in accordance with the following scheme:
147 147
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26)
Figure imgf000150_0001
SUBSTITUTE SHEET (RULE 26)
Figure imgf000150_0001
CH2CH2-Hal, CH=CH2, еtс
Figure imgf000150_0002
CH2CH2-Hal, CH = CH2, etc
Figure imgf000150_0002
в которой ArI, Аlkl, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Alkl, Rl, R2 and Q have the meanings defined above.
24. Способ получения соединений формулы 1.4 и 1.5 в соответствие со следующей схемой:  24. The method of obtaining compounds of formulas 1.4 and 1.5 in accordance with the following scheme:
еtс
Figure imgf000150_0003
etc
Figure imgf000150_0003
в которой ArI, Rl, R2 и Q имеют значения, определенные выше.  in which ArI, Rl, R2, and Q are as defined above.
148 148
ЗАМЕНЯЮЩИЙ ЛИСТ (ПРАВИЛО 26)  SUBSTITUTE SHEET (RULE 26)
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